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Journal articles on the topic 'Aza-Diels–Alder cycloadditions'

Author: Grafiati

Published: 25 May 2024

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1

Heredia-Moya, Jorge, Daniel A. Zurita, José Eduardo Cadena-Cruz, and Christian D. Alcívar-León. "Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis." Molecules 27, no. 19 (October 9, 2022): 6708. http://dx.doi.org/10.3390/molecules27196708.

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Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.

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2

Presset, Marc, Michel Rajzmann, Guillaume Dauvergne, Jean Rodriguez, and Yoann Coquerel. "Periselectivity in the Aza-Diels–Alder Reaction of 1-Azadienes with α-Oxoketenes: A Combined Experimental and Theoretical Study." Molecules 25, no. 20 (October 20, 2020): 4811. http://dx.doi.org/10.3390/molecules25204811.

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Inversions in the periselectivity of formal aza-Diels–Alder cycloadditions between α-oxoketenes generated by a thermally-induced Wolff rearrangement and 1-azadienes were observed experimentally as a function of the α-oxoketene and the 1-azadiene, as well as the reaction temperature and time. Some unexpected inversion in the diastereoselectivity was observed, too. These variations in selectivities were fully rationalized by computational modeling using density functional theory (DFT) methods.

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3

Skrzyńska, Anna, Sebastian Frankowski, and Łukasz Albrecht. "Cyclic 1‐Azadienes in the Organocatalytic Inverse‐Electron‐Demand Aza‐Diels‐Alder Cycloadditions." Asian Journal of Organic Chemistry 9, no. 11 (September 4, 2020): 1688–700. http://dx.doi.org/10.1002/ajoc.202000332.

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4

CHEMOURI, HAFIDA, WAFAA BENCHOUK, and SIDI MOHAMED MEKELLECHE. "REGIOSELECTIVITY OF HETERO DIELS–ALDER REACTIONS BETWEEN 1-AZA-1,3-BUTADIENE DERIVATIVES AND DIMETHYLVINYLAMINE: A THEORETICAL INVESTIGATION." Journal of Theoretical and Computational Chemistry 05, no. 04 (December 2006): 707–18. http://dx.doi.org/10.1142/s0219633606002581.

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The regioselectivity of hetero Diels–Alder reactions between 1-aza-1,3-butadiene derivatives and dimethylvinylamine is elucidated by means of several theoretical approaches, namely, the Gazquez–Mendez rule based on the calculation of local softnesses, barrier activation calculations, maximum hardness principle, and the Houk rule based on the FMO theory. The calculations were performed at the B3LYP/6-31G(d) level of theory, and the obtained results are in agreement with available experimental results. Moreover, the present analysis shows that these inverse electron demand polar cycloadditions present a linear relationship between the activation barriers of the favored ortho regio-isomers and the inverse of electrophilicity differences of the reagents.

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5

Sousa, Carlos A. D., M. Luísa C. Vale, José E. Rodríguez-Borges, Xerardo Garcia-Mera, and Jesús Rodríguez-Otero. "Acid-catalyzed aza-Diels–Alder versus 1,3-dipolar cycloadditions of methyl glyoxylate oxime with cyclopentadiene." Tetrahedron Letters 49, no. 40 (September 2008): 5777–81. http://dx.doi.org/10.1016/j.tetlet.2008.07.110.

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6

Mayr, Herbert, Armin R. Ofial, Jürgen Sauer, and Bernhard Schmied. "[2++4] Cycloadditions of Iminium Ions − Concerted or Stepwise Mechanism of Aza Diels−Alder Reactions?" European Journal of Organic Chemistry 2000, no. 11 (June 2000): 2013–20. http://dx.doi.org/10.1002/1099-0690(200006)2000:11<2013::aid-ejoc2013>3.0.co;2-a.

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7

Blanco-Carapia, Roberto E., Enrique A. Aguilar-Rangel, Mónica A. Rincón-Guevara, Alejandro Islas-Jácome, and Eduardo González-Zamora. "Synthesis of New Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via an Ugi-Zhu/Cascade/Click Strategy." Molecules 28, no. 10 (May 14, 2023): 4087. http://dx.doi.org/10.3390/molecules28104087.

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A diversity-oriented synthesis (DOS) of two new polyheterocyclic compounds was performed via an Ugi-Zhu/cascade (N-acylation/aza Diels-Alder cycloaddition/decarboxylation/dehydration)/click strategy, both step-by-step to optimize all involved experimental stages, and in one pot manner to evaluate the scope and sustainability of this polyheterocyclic-focused synthetic strategy. In both ways, the yields were excellent, considering the high number of bonds formed with release of only one carbon dioxide and two molecules of water. The Ugi-Zhu reaction was carried out using the 4-formylbenzonitrile as orthogonal reagent, where the formyl group was first transformed into the pyrrolo[3,4-b]pyridin-5-one core, and then the remaining nitrile group was further converted into two different nitrogen-containing polyheterocycles, both via click-type cycloadditions. The first one used sodium azide to obtain the corresponding 5-substituted-1H-tetrazolyl-pyrrolo[3,4-b]pyridin-5-one, and the second one with dicyandiamide to synthesize the 2,4-diamino-1,3,5-triazine-pyrrolo[3,4-b]pyridin-5-one. Both synthesized compounds may be used for further in vitro and in silico studies because they contain more than two heterocyclic moieties of high interest in medicinal chemistry, as well as in optics due to their high π-conjugation.

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8

Fillion, Houda, Félix Pautet, Pascal Nebois, and Zouhair Bouaziz. "Cycloadditions of α,β-Unsaturated N,N-Dimethylhydrazones. A Diels-Alder Strategy for the Building of Aza-Hetero Rings." HETEROCYCLES 54, no. 2 (2001): 1095. http://dx.doi.org/10.3987/rev-00-sr(i)5.

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9

Ntirampebura, Deogratias, and Léon Ghosez. "Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives." Tetrahedron Letters 40, no. 39 (September 1999): 7079–82. http://dx.doi.org/10.1016/s0040-4039(99)01444-6.

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10

Palacios, Francisco, Concepción Alonso, Patricia Amezua, and Gloria Rubiales. "Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels−Alder Cycloadditions of Neutral 2-Azadienes." Journal of Organic Chemistry 67, no. 6 (March 2002): 1941–46. http://dx.doi.org/10.1021/jo016325v.

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11

Skrzyńska, Anna, Sebastian Frankowski, and Łukasz Albrecht. "Front Cover: Cyclic 1‐Azadienes in the Organocatalytic Inverse‐Electron‐Demand Aza‐Diels‐Alder Cycloadditions (Asian J. Org. Chem. 11/2020)." Asian Journal of Organic Chemistry 9, no. 11 (November 2020): 1665. http://dx.doi.org/10.1002/ajoc.202000528.

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12

Pautet, Felix, Pascal Nebois, Zouhair Bouaziz, and Houda Fillion. "ChemInform Abstract: Cycloadditions of α,β-Unsaturated N,N-Dimethylhydrazones. A Diels-Alder Strategy for the Building of Aza-hetero Rings." ChemInform 32, no. 21 (May 26, 2010): no. http://dx.doi.org/10.1002/chin.200121258.

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13

Palacios, Francisco, Concepcion Alonso, Patricia Amezua, and Gloria Rubiales. "ChemInform Abstract: Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels-Alder Cycloadditions of Neutral 2-Azadienes." ChemInform 33, no. 34 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200234164.

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14

Ntirampebura, Deogratias, and Leon Ghosez. "ChemInform Abstract: Cycloadditions of 2-Aza-1,3-dienes to Aldehydes: A Diels-Alder Strategy for the Diastereoselective Hydroxyalkylation of Carboxylic Acid Derivatives." ChemInform 30, no. 48 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199948163.

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15

Hamzik, Philip J., Anne-Sophie Goutierre, Takeo Sakai, and Rick L. Danheiser. "Aza Diels–Alder Reactions of Nitriles, N,N-Dimethylhydrazones, and Oximino Ethers. Application in Formal [2 + 2 + 2] Cycloadditions for the Synthesis of Pyridines." Journal of Organic Chemistry 82, no. 24 (December 2017): 12975–91. http://dx.doi.org/10.1021/acs.joc.7b02503.

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16

ABRAHAM, H., E. THEUS, and L. STELLA. "ChemInform Abstract: Synthesis of Picolinic Acid Derivatives via Aza Diels-Alder Reaction: Zinc Iodide Activated Cycloadditions Between Methyl N-(1-Phenylethyl)-. alpha.-iminoacetate and Electron Rich Dienes." ChemInform 26, no. 14 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199514044.

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17

Ye, Rong, Jing Sun, Ying Han, and Chao-Guo Yan. "Molecular diversity of TEMPO-mediated cycloaddition of ketohydrazones and 3-phenacylideneoxindoles." New Journal of Chemistry 45, no. 11 (2021): 5075–80. http://dx.doi.org/10.1039/d0nj06036d.

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18

Back, Thomas G. "Design and synthesis of some biologically interesting natural and unnatural products based on organosulfur and selenium chemistry." Canadian Journal of Chemistry 87, no. 12 (December 2009): 1657–74. http://dx.doi.org/10.1139/v09-133.

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Organosulfur and selenium chemistry has provided fertile ground for the discovery of novel synthetic methodology and for the design of bioactive molecules with potential therapeutic applications. Thus, acetylenic sulfones have been employed in novel strategies for the synthesis of nitrogen heterocycles, including several biologically active alkaloids. The conjugate addition of nitrogen nucleophiles containing ester or chloroalkyl substituents to acetylenic sulfones was followed by base-mediated intramolecular alkylation or acylation to afford variously substituted piperidines, pyrrolizidines, indolizidines, quinolizidines, decahydroquinolines, and 4-quinolones. The products include the dendrobatid alkaloids (–)-pumiliotoxin C, indolizidines (–)-167B, 207A, 209B, and 209D, as well as (–)-(ent)-julifloridine, (–)-lasubine II, myrtine, and two recently discovered alkaloids from the medicinal plant Ruta chalepensis , which had not been previously synthesized. Acetylenic sulfones were also incorporated on solid supports and employed in the types of cyclizations mentioned above, as well as for Diels–Alder reactions and a large variety of 1,3-dipolar cycloadditions. Conjugate additions of tertiary cyclic α-vinyl amines to acetylenic sulfones generated zwitterions that underwent exceptionally facile formal aza-Cope rearrangements to afford ring-expanded macrocyclic amines. An iterative version was developed and used in the synthesis of motuporamine A and B. With respect to organoselenium chemistry, two classes of compounds are described that function as novel mimetics of the selenoenzyme glutathione peroxidase (GPx), which protects cells from oxidative stress caused by the formation of peroxides during aerobic metabolism. They include cyclic seleninates and spirodioxyselenuranes, both of which efficiently catalyze the reduction of peroxides with thiols and are of potential value in the mitigation of oxidative stress. Their aromatic derivatives are generally less effective catalysts, but substituent effects can be used to modulate their activities. The mechanism of their catalytic cycles has been elucidated and Hammett plots indicate that the oxidation of Se(II) to Se(IV) is the rate-determining step for both classes. A methoxy-substituted aromatic spirodioxyselenurane provided the fastest rate for a small-molecule selenium compound that we have observed to date for the reduction of hydrogen peroxide with benzyl thiol.

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19

Ayadi, Sameh, and Manef Abderrabba. "Étude DFT des réactions de cycloaddition de type Diels–Alder sur le 4-aza-6-nitrobenzofuroxane." Canadian Journal of Chemistry 85, no. 5 (May 1, 2007): 331–35. http://dx.doi.org/10.1139/v07-026.

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The purpose of this work is a theoretical study of Diels–Alder reactions between the 4-aza-6-nitrobenzofuroxan 1 with a series of dienophiles 3a–3c. From a thermodynamic and orbital point of view, we discuss the reactivity and the stereoselectivty of these reactions. Activation barriers in the Diels-Alder reactions of compound 1 with a series of dienophiles 3a–3c have been calculated and discussed.Key words: inverse electron demand Diels–Alder (IEDDA), DFT method, 4-aza-6-nitrobenzofuroxane.

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20

Zhang, Xiaofeng, Gagan Dhawan, Alex Muthengi, Shuai Liu, Wei Wang, Marc Legris, and Wei Zhang. "One-pot and catalyst-free synthesis of pyrroloquinolinediones and quinolinedicarboxylates." Green Chemistry 19, no. 16 (2017): 3851–55. http://dx.doi.org/10.1039/c7gc01380a.

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A method for the catalyst-free synthesis of pyrroloquinolinediones and quinolinedicarboxylates is developed through a one-pot synthesis involving denitrogenation of azide, benzisoxazole formation, aza-Diels–Alder cycloaddition, and dehydrative aromatization.

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21

Vázquez-Vera, Óscar, Daniel Segura-Olvera, Mónica Rincón-Guevara, Atilano Gutiérrez-Carrillo, Miguel García-Sánchez, Ilich Ibarra, Leticia Lomas-Romero, Alejandro Islas-Jácome, and Eduardo González-Zamora. "Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization." Molecules 23, no. 8 (August 14, 2018): 2029. http://dx.doi.org/10.3390/molecules23082029.

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A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.

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22

Wu, Xiang, Shi-Bao Zhao, Lang-Lang Zheng, and You-Gui Li. "Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones." Molecules 23, no. 9 (September 1, 2018): 2228. http://dx.doi.org/10.3390/molecules23092228.

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Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels–Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products.

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23

Kumar, Kamal, Mohammad Rehan, Jana Flegel, Franziska Heitkamp, Jorgelina L. Pergomet, Felix Otte, and Carsten Strohmann. "Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators." Synthesis 52, no. 21 (August 10, 2020): 3140–52. http://dx.doi.org/10.1055/s-0040-1707222.

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An enantioselective hetero-Diels–Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N,N′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo-Cycloadducts formed via stereospecific cycloaddition with Z-olefin displayed potent activity in modulation of hedgehog pathway.

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24

Escalante, Carlos H., Eder I. Martínez-Mora, Carlos Espinoza-Hicks, Alejandro A. Camacho-Dávila, Fernando R. Ramos-Morales, Francisco Delgado, and Joaquín Tamariz. "Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole." Beilstein Journal of Organic Chemistry 16 (June 17, 2020): 1320–34. http://dx.doi.org/10.3762/bjoc.16.113.

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A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.

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25

Fochi, Mariafrancesca, Luca Bernardi, and Lorenzo Caruana. "Catalytic Asymmetric Aza-Diels–Alder Reactions: The Povarov Cycloaddition Reaction." Synthesis 46, no. 02 (December 10, 2013): 135–57. http://dx.doi.org/10.1055/s-0033-1338581.

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26

Islas-Jácome, Perla, Cecilia García-Falcón, Sandra L. Castañón-Alonso, Ernesto Calderón-Jaimes, Daniel Canseco-González, Alejandro Islas-Jácome, and Eduardo González-Zamora. "2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one." Molbank 2023, no. 3 (July 10, 2023): M1693. http://dx.doi.org/10.3390/m1693.

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The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (1H, 13C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS.

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27

Morales-Salazar, Ivette, Mónica A. Rincón-Guevara, Eduardo González-Zamora, and Alejandro Islas-Jácome. "2-Benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one." Molbank 2022, no. 4 (November 23, 2022): M1503. http://dx.doi.org/10.3390/m1503.

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The new polyheterocyclic compound 2-benzyl-3-morpholino-7-(thiophen-2-yl)-6-(thiophen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (1) was synthesized via a one-pot process involving an Ugi-Zhu three-component reaction coupled to a cascade aza-Diels-Alder cycloaddition/N-acylation/decarboxylation/dehydration process, using toluene as the solvent, ytterbium (III) triflate as the Lewis acid catalyst, and microwave-dielectric heating to increase the overall yield by up to 73%, while decreasing the reaction time to less than one hour. Product 1 was fully characterized by its physicochemical properties and using spectroscopic techniques (IR, HRMS and NMR).

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28

Frankowski, Sebastian, Anna Skrzyńska, Lesław Sieroń, and Łukasz Albrecht. "Deconjugated‐Ketone‐Derived Dienolates in Remote, Stereocontrolled, Aromative aza ‐Diels‐Alder Cycloaddition." Advanced Synthesis & Catalysis 362, no. 13 (May 5, 2020): 2658–65. http://dx.doi.org/10.1002/adsc.202000197.

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29

Fochi, Mariafrancesca, Lorenzo Caruana, and Luca Bernardi. "ChemInform Abstract: Catalytic Asymmetric Aza-Diels-Alder Reactions: The Povarov Cycloaddition Reaction." ChemInform 45, no. 15 (March 27, 2014): no. http://dx.doi.org/10.1002/chin.201415264.

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30

Barešić, Luka, Davor Margetić, and Zoran Glasovac. "Anion-Controlled Synthesis of Novel Guanidine-Substituted Oxanorbornanes." International Journal of Molecular Sciences 23, no. 24 (December 16, 2022): 16036. http://dx.doi.org/10.3390/ijms232416036.

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The cycloaddition of simple alkyl-substituted guanidine derivatives is an interesting approach toward polycyclic superbases and guanidine-based organocatalysts. Due to the high nucleophilicity of guanidines, an aza-Michael reaction with dienophiles is more common and presents a huge obstacle in achieving the desired synthetic goal. Our preliminary investigations indicated that the proton could act as a suitable protecting group to regulate the directionality of the reaction. To investigate the role of the protonation state and type of anion, the reactivity of furfuryl guanidines with dimethyl acetylenedicarboxylate was explored. Furfuryl guanidines showed a strong reaction dependence on the nucleophilicity of the counterion and the structure of guanidine. While the reaction of DMAD with the guanidinium halides provided products of an aza-Michael addition, Diels–Alder cycloaddition occurred if non-nucleophilic hexafluorophosphate salts were used. Depending on the structure and the reaction conditions, oxanorbornadiene products underwent subsequent intramolecular cyclization. A tendency toward intramolecular cyclization was interpreted in terms of the pKa of different positions of the guanidine functionality in oxanorbornadienes. New polycyclic guanidines had a slightly decreased pKa in acetonitrile and well-defined geometry suitable for the buildup of selective sensors.

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31

Rentería-Gómez, Manuel A., Shrikant G. Pharande, Alejandro Islas-Jácome, Eduardo González-Zamora, and Rocío Gámez-Montaño. "MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization." Proceedings 9, no. 1 (November 14, 2018): 5. http://dx.doi.org/10.3390/ecsoc-22-05779.

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An efficient Microwave (MW)-assisted synthesis of eight new 6-nitrilmethyl-pyrrolo[3,4-b]pyridin-5-ones via a domino process: aza Diels–Alder/N-acylation/aromatization (dehydration–decarboxylation) from their corresponding 2-aminonitrile-oxazoles and maleic anhydride are described. The use of MW as a heat source and scandium (III) triflate as a catalyst to promote the cycloaddition process was crucial to construct these polyfunctionalized products in very good yields (51–79%), considering both their molecular complexity and that only one domino-type experimental procedure was required for their synthesis. It is worth noting that all products reported herein have not been synthesized nor isolated anywhere. However, they can be of high interest for the synthetic and medicinal chemistry community because pyrrolo[3,4-b]pyridin-5-one is the structural core of various bioactive compounds. In the same context, it can be considered as a privileged aza analogue of the isoindolin-1-one, which in turn is the core of numerous anticancer agents.

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32

Khramtsova, Ekaterina E., Aleksandr D. Krainov, Maksim V. Dmitriev, and Andrey N. Maslivets. "Cycloaddition of 4-Acyl-1H-pyrrole-2,3-diones Fused at [e]-Side and Cyanamides: Divergent Approach to 4H-1,3-Oxazines." Molecules 27, no. 16 (August 17, 2022): 5257. http://dx.doi.org/10.3390/molecules27165257.

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4-Acyl-1H-pyrrole-2,3-diones fused at [e]-side with a heterocyclic moiety are suitable platforms for the development of a hetero-Diels–Alder-reaction-based, diversity-oriented approaches to series of skeletally diverse heterocycles. These platforms are known to react as oxa-dienes with dienophiles to form angular 6/6/5/6-tetracyclic alkaloid-like heterocycles and are also prone to decarbonylation at high temperatures resulting in generation of acyl(imidoyl)ketenes, bidentate aza- and oxa-dienes, which can react with dienophiles to form skeletally diverse products (angular tricyclic products or heterocyclic ensembles). Based on these features, we have developed an approach to two series of skeletally diverse 4H-1,3-oxazines (tetracyclic alkaloid-like 4H-1,3-oxazines and 5-heteryl-4H-1,3-oxazines) via a hetero-Diels–Alder reaction of 4-acyl-1H-pyrrole-2,3-diones fused at [e]-side with cyanamides. The products of these transformations are of interest for drug discovery, since compounds bearing 4H-1,3-oxazine moiety are extensively studied for inhibitory activities against anticancer targets.

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33

Barluenga, José, Francisco J. González, Santos Fustero, and Vicente Gotor. "Diels–Alder cycloaddition reaction of unactivated 2-aza-1,3-dienes with dialkyl azodicarboxylates and heterocumulenes." J. Chem. Soc., Chem. Commun., no. 15 (1986): 1179–80. http://dx.doi.org/10.1039/c39860001179.

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34

Morales-Salazar, Ivette, Carlos E. Garduño-Albino, Flora P. Montes-Enríquez, Dania A. Nava-Tapia, Napoleón Navarro-Tito, Leonardo David Herrera-Zúñiga, Eduardo González-Zamora, and Alejandro Islas-Jácome. "Synthesis of Pyrrolo[3,4-b]pyridin-5-ones via Ugi–Zhu Reaction and In Vitro–In Silico Studies against Breast Carcinoma." Pharmaceuticals 16, no. 11 (November 6, 2023): 1562. http://dx.doi.org/10.3390/ph16111562.

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An Ugi–Zhu three-component reaction (UZ-3CR) coupled in a one-pot manner to a cascade process (N-acylation/aza Diels–Alder cycloaddition/decarboxylation/dehydration) was performed to synthesize a series of pyrrolo[3,4-b]pyridin-5-ones in 20% to 92% overall yields using ytterbium triflate as a catalyst, toluene as a solvent, and microwaves as a heat source. The synthesized molecules were evaluated in vitro against breast cancer cell lines MDA-MB-231 and MCF-7, finding that compound 1f, at a concentration of 6.25 μM, exhibited a potential cytotoxic effect. Then, to understand the interactions between synthesized compounds and the main proteins related to the cancer cell lines, docking studies were performed on the serine/threonine kinase 1 (AKT1) and Orexetine type 2 receptor (Ox2R), finding moderate to strong binding energies, which matched accurately with the in vitro results. Additionally, molecular dynamics were performed between proteins related to the studied cell lines and the three best ligands.

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35

Lepifre, Franck, Christophe Buon, Pierre-Yves Roger, Pascal Bouyssou, and Gérard Coudert. "Easy access to N-aryl, N-heteroarylbenzoxazolinones and 4-aza analogues via Diels–Alder cycloaddition reactions." Tetrahedron Letters 45, no. 44 (October 2004): 8257–59. http://dx.doi.org/10.1016/j.tetlet.2004.08.162.

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36

Makino, Kazuishi, Yoshiaki Henmi, Makiko Terasawa, Osamu Hara, and Yasumasa Hamada. "Remarkable effects of titanium tetrachloride in diastereoselective aza Diels–Alder cycloaddition: synthesis of (S)-piperazic acid." Tetrahedron Letters 46, no. 4 (January 2005): 555–58. http://dx.doi.org/10.1016/j.tetlet.2004.12.003.

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37

González-Zamora, Eduardo, Alejandro Islas-Jácome, Atilano Gutiérrez-Carrillo, and Miguel García-Garibay. "One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels–Alder Cycloaddition." Synlett 25, no. 03 (December 2, 2013): 403–6. http://dx.doi.org/10.1055/s-0033-1340218.

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38

Vil', Vera A., Sergei S. Grishin, Elena P. Baberkina, Anna L. Alekseenko, Alexey P. Glinushkin, Alexey E. Kovalenko, and Alexander O. Terent'ev. "Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition." Advanced Synthesis & Catalysis 364, no. 6 (January 20, 2022): 1098–108. http://dx.doi.org/10.1002/adsc.202101355.

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39

Kiran, I. N. Chaithanya, R. Santhosh Reddy, Chandraiah Lagishetti, Huacheng Xu, Zhen Wang, and Yun He. "Selective Aza Diels–Alder and Domino [4+2]/[2+2] Cycloaddition Reactions of Arynes with N-Sulfonyl Ketimines." Journal of Organic Chemistry 82, no. 3 (January 26, 2017): 1823–32. http://dx.doi.org/10.1021/acs.joc.6b02667.

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40

Islas-Jacome, Alejandro, Atilano Gutierrez-Carrillo, Miguel A. Garcia-Garibay, and Eduardo Gonzalez-Zamora. "ChemInform Abstract: One-Pot Synthesis of Nuevamine Aza-Analogues by Combined Use of an Oxidative Ugi Type Reaction and Aza-Diels-Alder Cycloaddition." ChemInform 45, no. 30 (July 10, 2014): no. http://dx.doi.org/10.1002/chin.201430162.

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41

Cuerva, Juan M., Diego J. Cárdenas, and Antonio M. Echavarren. "Intramolecular Michael-type addition of azadienes to 1,4-naphthoquinones instead of Aza-Diels–Alder cycloaddition: a synthesis of ascididemin." Journal of the Chemical Society, Perkin Transactions 1, no. 11 (May 10, 2002): 1360–65. http://dx.doi.org/10.1039/b202555h.

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42

Boger, Dale L., Wendy L. Corbett, and J. Mark Wiggins. "Room-temperature, endo-specific 1-aza-1,3-butadiene Diels-Alder reactions: acceleration of the LUMOdiene-controlled [4 + 2] cycloaddition reactions through noncomplementary aza diene substitution." Journal of Organic Chemistry 55, no. 10 (May 1990): 2999–3000. http://dx.doi.org/10.1021/jo00297a006.

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43

Saito, Takao, Satoru Kobayashi, Takashi Otani, Hideoki Iwanami, and Takayuki Soda. "Diene-Transmissive Hetero-Diels-Alder Cycloaddition Using Cross-Conjugated Dioxatrienes: A Novel Synthesis of Tetrahydropyran-Fused Aza- and Thia-heterocycles." HETEROCYCLES 76, no. 1 (2008): 227. http://dx.doi.org/10.3987/com-08-s(n)55.

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44

Morales-Salazar, Ivette, Carlos E. Garduño-Albino, Flora P. Montes-Enríquez, Atilano Gutiérrez-Carrillo, Yareli Rojas-Aguirre, Nancy Viridiana Estrada-Toledo, Jorge Sandoval-Basilio, et al. "In Vitro and In Silico Studies of Bis-furyl-pyrrolo[3,4-b]pyridin-5-ones on Dengue Virus." Journal of the Mexican Chemical Society 68, no. 1 (January 1, 2024): 170–83. http://dx.doi.org/10.29356/jmcs.v68i1.2103.

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A series of six bis-furyl-pyrrolo[3,4-b]pyridin-5-ones synthesized via an Ugi-Zhu reaction coupled to a cascade process [aza Diels-Alder cycloaddition/N-acylation/aromatization] were evaluated in vitro against Dengue virus serotype 4 infection, and the Dengue virus replicon system encoding a Renilla luciferase gen reporter. Also, in silico studies on the non-structural protein 3 (NS3), a flavivirus protease comprising an attractive target for development of therapeutic antivirals bound to non-structural protein 2B (NS3-NS2B) were performed. The in vitro results showed that compounds 1a and 1b reduced the expression of Renilla luciferase in 44.2 and 31.6%, respectively. Additionally, the same compounds decreased viral load, thus revealing their potential activity against Dengue virus serotype 4. From in silico simulations, it was developed a NS3-NS2B model, which was used as a target for the studied molecules. Computational results agree with experimental data, showing that 1a is the best ligand. Finally, a pharmacophoric model was computed for NS3-NS2B, which shows that the ligands need two hydrophobic and one hydrophilic fragment. Such results suggest that two out of the six synthesized bis-furyl-pyrrolo[3,4-b]pyridin-5-ones derivatives presents potential antiviral activity against Dengue virus in vitro. Resumen. Una serie de seis bis-furil-pirrolo[3,4-b]piridin-5-onas sintetizadas vía una reacción Ugi-Zhu acoplada a un proceso en cascada [cicloadición aza Diels-Alder/N-acilación/aromatización] fueron evaluadas in vitro contra infección por el serotipo 4 del virus del dengue y el sistema de replicón del virus del Dengue que codifica un gen reportero de la luciferasa de la Renilla. Además, se realizaron estudios in silico sobre la proteína no estructural 3 (NS3), una proteasa de flavivirus que comprende un blanco atractivo para el desarrollo de antivirales terapéuticos unidos a la proteína no estructural 2B (NS3-NS2B). Los estudios in vitro revelaron que los compuestos 1a y 1b reducen la expresión de Renilla luciferasa en un 44.2 y 31.6%, respectivamente. Adicionalmente, estos compuestos redujeron la carga viral, revelando así su actividad potencial contra el virus del Dengue serotipo 4. Derivado de las simulaciones in silico, se obtuvo un modelo homólogo para NS3-NS2B, el cual fue considerado como blanco de las moléculas estudiadas. Los resultados computacionales correlacionan con los experimentales, mostrando que 1a es el mejor ligando. Finalmente, se generó un modelo farmacofórico para NS3-NS2B, el cual muestra que los ligandos necesitan dos fragmentos hidrofóbicos y uno hidrofílico. Estos resultados demuestran que dos de los seis compuestos que se estudiaron presentan actividad antiviral in vitro.

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45

Sasaki, Michiko, Philip J. Hamzik, Hidaka Ikemoto, Samuel G. Bartko, and Rick L. Danheiser. "Formal Bimolecular [2 + 2 + 2] Cycloaddition Strategy for the Synthesis of Pyridines: Intramolecular Propargylic Ene Reaction/Aza Diels–Alder Reaction Cascades." Organic Letters 20, no. 19 (September 24, 2018): 6244–49. http://dx.doi.org/10.1021/acs.orglett.8b02728.

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46

Castillo, Juan-Carlos, Brian Castro Agudelo, Jaime Gálvez, Yannick Carissan, Jean Rodriguez, and Yoann Coquerel. "Periselectivity in the aza-Diels–Alder Cycloaddition between α-Oxoketenes and N-(5-Pyrazolyl)imines: A Combined Experimental and Theoretical Study." Journal of Organic Chemistry 85, no. 11 (May 12, 2020): 7368–77. http://dx.doi.org/10.1021/acs.joc.0c00767.

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47

Cuerva, Juan M., Diego J. Cardenas, and Antonio M. Echavarren. "ChemInform Abstract: Intramolecular Michael-Type Addition of Azadienes to 1,4-Naphthoquinones Instead of Aza-Diels-Alder Cycloaddition: A Synthesis of Ascididemin." ChemInform 33, no. 40 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200240216.

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48

Boger, Dale L., and Timothy T. Curran. "Diels-Alder reactions of 1-aza-1,3-butadienes: room temperature, endo-selective LUMOdiene-controlled [4 + 2] cycloaddition reactions of N-sulfonyl-4-(ethoxycarbonyl)-1-aza-1,3-butadienes." Journal of Organic Chemistry 55, no. 20 (September 1990): 5439–42. http://dx.doi.org/10.1021/jo00307a009.

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49

Singal, Kewal Krishan, Baldev Singh, and Baldev Raj. "Studies in 1-Aza-1,3-butadienes: Diels-Alder Cycloaddition Reactions of 1,4-Diaryl-1-aza-1,3-butadienes with Aryl Sulphonyl Nitrosites Leading to the Synthesis of New Oxadiazines." Synthetic Communications 23, no. 1 (January 1993): 107–14. http://dx.doi.org/10.1080/00397919308020408.

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50

Cheng, Yea Shun, Eugene Ho, Patrick S. Mariano, and Herman L. Ammon. "Mechanistic aspects of the boron trifluoride catalyzed, intermolecular Diels-Alder cycloaddition of an unactivated 2-aza 1,3-diene with electron-donating-substituted dienophiles." Journal of Organic Chemistry 50, no. 26 (December 1985): 5678–86. http://dx.doi.org/10.1021/jo00350a049.

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