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Journal articles on the topic 'Cycloaddition of pyrroles'

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Published: 22 July 2024

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1

Hu, Fan, Jerome Ng, and Pauline Chiu. "Pyrroles as Dienes in (4+3) Cycloadditions." Synthesis 51, no. 05 (February 6, 2019): 1073–86. http://dx.doi.org/10.1055/s-0037-1611660.

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This short review summarizes the examples to date of successful (4+3) cycloadditions, including formal (4+3) cycloadditions, where pyrrole derivatives reacted as the diene component, to provide aza-bridged bicyclic and polycyclic adducts.1 Introduction2 Unsubstituted Pyrroles as Dienes in (4+3) Cycloadditions3 C-Substituted Pyrroles as Dienes in (4+3) Cycloadditions4 Intramolecular Pyrrole (4+3) Cycloadditions5 Conclusions

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2

Gao, Meng, Wenting Zhao, Hongyi Zhao, Ziyun Lin, Dongfeng Zhang, and Haihong Huang. "An efficient and facile access to highly functionalized pyrrole derivatives." Beilstein Journal of Organic Chemistry 14 (April 20, 2018): 884–90. http://dx.doi.org/10.3762/bjoc.14.75.

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A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

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3

Li, Jin-Heng, De-Lie An, and Jing-Hao Qin. "Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles." Synthesis 52, no. 24 (October 13, 2020): 3818–36. http://dx.doi.org/10.1055/s-0040-1707355.

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Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spiroheterocyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook

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4

Sleziak, Róbert, and Alžbeta Krutošíková. "Cycloaddition Reactions of Furo[2,3-b]pyrroles." Collection of Czechoslovak Chemical Communications 64, no. 2 (1999): 321–28. http://dx.doi.org/10.1135/cccc19990321.

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Reactions of furo[2,3-b]pyrroles with dimethyl butynedioate and ethyl propynoate were investigated. The reaction course is influenced by the substituents on the fused system. Products of [4+2]cycloaddition to the furan ring leading to indole derivatives have been observed. In the case of the reaction of methyl 6H-furo[2,3-b]pyrrole-5-carboxylate (1a) with dimethyl butynedioate, products of [4+2]cycloaddition to the furan ring as well as of Michael addition to the pyrrole ring leading to N-substituted indole derivative 3 have been observed.

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5

Motornov, Vladimir A., Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, and Sema L. Ioffe. "Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles." Organic & Biomolecular Chemistry 19, no. 15 (2021): 3413–27. http://dx.doi.org/10.1039/d1ob00146a.

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6

Krutošíková, Alžbeta. "Synthesis and reactions of condensed furan derivatives." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 597–621. http://dx.doi.org/10.1135/cccc19900597.

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Synthesis of heterocyclic compounds containing a fused furan ring was studied. Substitution, addition and cycloaddition reactions of furo[3,2-b]pyrroles and their condensed derivatives involving the interesting transformations of furo[3,2-b]pyrrole system are presented.

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7

Guo, Tenglong, Quanbin Jiang, and Zhengkun Yu. "Palladium-catalyzed oxidative annulation of in situ generated enones to pyrroles: a concise route to functionalized indoles." Organic Chemistry Frontiers 2, no. 10 (2015): 1361–65. http://dx.doi.org/10.1039/c5qo00203f.

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Pd(ii)-catalyzed, Cu(ii)-mediated indole synthesis from pyrroles and 3-chloropropiophenones has been efficiently achieved. In-situ generated enones were employed for the establishment of a benzene ring onto a pyrrole backbone via dehydrochlorination/C–H olefination/cycloaddition/dehydrogenative aromatization.

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8

Krutošíková, Alžbeta, Miloslava Dandárová, Juraj Alföldi, and Jaroslav Kováč. "Addition and cycloaddition reactions of furo[3,2-b]pyrroles and their benzo[b] analogues: An NMR study of structure of products." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1770–78. http://dx.doi.org/10.1135/cccc19881770.

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Reaction of furo[3,2-b]pyrroles and their benzo[b] analogues with dimethyl butynedioate and ethyl propyonate were investigated. The reaction course is influenced by substituents on the system. Products of [4 + 2] cycloaddition to the furan or pyrrole nucleus as well as products of Michael addition to the benzo[b]furo[3,2-b]pyrrole system have been found. The structure of the products has been proven by 1H NMR and 13C NMR spectroscopy.

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9

Lakhlifi, Tahar, Ahmed Sedqui, Toufik Fathi, Bernard Laude, and Jean-François Robert. "Double diastéréosélectivité de la cycloaddition dipolaire-1,3 d'ylures d'azométhine cycliques substitués." Canadian Journal of Chemistry 72, no. 6 (June 1, 1994): 1417–23. http://dx.doi.org/10.1139/v94-178.

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Seven derivatives of methyl 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylates 1 were synthetized. These compounds are precursors of pentagonal cyclic azomethine ylids, the two sides of which are diastereotopic. The 1,3-dipolar species react with N-methyl and N-phenylmaleimides diastereospecifically. The approach of the reactant species occurs from the less hindered side of the 1,3-dipole and in endo to lead the thermodynamically stable exo cycloadduct. Moreover, oxidation of the compounds 1 gives the corresponding substituted pyrroles.

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10

Zhou, Kai, Ming Bao, Jingjing Huang, Zhenghui Kang, Xinfang Xu, Wenhao Hu, and Yu Qian. "Iron-catalyzed [3 + 2]-cycloaddition of in situ generated N-ylides with alkynes or olefins: access to multi-substituted/polycyclic pyrrole derivatives." Organic & Biomolecular Chemistry 18, no. 3 (2020): 409–14. http://dx.doi.org/10.1039/c9ob02571e.

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An iron-catalyzed three-component reaction of benzimidazoles with diazoacetates and electron-deficient alkynes or alkenes that delivers multi-substituted pyrroles, pyrrolo[1,2-a]benzimidazoles and pyrrolo[1,2-a] quinoxalinones has been reported.

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11

Lin, Zhang-qi, Chao-dong Li, Zi-chun Zhou, Shuai Xue, Jian-rong Gao, Qing Ye, and Yu-jin Li. "Copper(II)-Promoted Oxidation/[3+2]Cycloaddition/Aromatization Cascade: Efficient Synthesis of Tetrasubstituted NH-Pyrrole from Chalcones and Iminodiacetates." Synlett 30, no. 12 (June 12, 2019): 1442–46. http://dx.doi.org/10.1055/s-0039-1689972.

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A simple and highly efficient method for the preparation of tetrasubstituted NH-pyrrole from a wide range of chalcones and diethyl iminodiacetates via a Cu(OAc)2-promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction has been developed. This reaction proceeds through dehydrogenations, deamination, and oxidative cyclization, affording the corresponding products in good to excellent yields. This convenient methodology for constructing tetrasubstituted NH-pyrroles has several advantages over existing methods, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions. A wide range of substrates are tolerated.

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12

Li, Chengjie, Martin Fechtel, Yaqing Feng, and Bernhard Kräutler. "Corroles programmed for regioselective cycloaddition chemistry — synthesis of a bisadduct with C60-fullerene." Journal of Porphyrins and Phthalocyanines 16, no. 05n06 (May 2012): 556–63. http://dx.doi.org/10.1142/s108842461250054x.

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A symmetrical β,β′-tetrasulfoleno-corrole is described here as an excellent and selective precursor to highly reactive corrole-β,β′-dienes, opening a selective route to specific β,β′-functionalized corroles via cycloaddition chemistry. The β,β′-tetrasulfoleno-corrole was prepared by acid catalyzed condensation of tolylaldehyde and a β,β′-disulfoleno-dipyrromethane, which was obtained by standard procedures. Crystalline deep green β,β′-tetrasulfoleno-corrole was isolated in 8–10% yield. Thermolysis of the corrole at 140 °C and in presence of an excess of C60 -fullerene gave a difullereno-corrole selectively (> 80% yield). The spectroscopic data indicated attachment of the two fullerene units at the "western," directly connected pyrrole rings. The tetrasulfoleno-corrole thus showed a remarkable preference for loss of sulphur dioxide and subsequent cycloaddition at the two "western" rings. In the difullereno-adduct, two sulfolene groups in the remaining "eastern" β,β″-disulfoleno-pyrroles still are available as "caged dienes" for further thermal diene formation, and attachment of additional groups via [4 + 2]-cycloaddition reactions.

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13

Gribble, G. W. "Novel chemistry of indole in the synthesis of heterocycles." Pure and Applied Chemistry 75, no. 10 (January 1, 2003): 1417–32. http://dx.doi.org/10.1351/pac200375101417.

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Indoles that are substituted at the 2- or 3-position with electron-withdrawing groups (nitro, phenylsulfonyl) undergo nucleophilic addition, 1,3-dipolar cycloaddition, and Diels–Alder reactions to give a variety of indoles, pyrroloindoles, and carbazoles. New methods for the synthesis of furo[3,4-b]indoles and the novel ring system furo[3,4-b]pyrrole are described for the first time. Diels–Alder reactions of furo[3,4-b]pyrroles afford indoles after dehydration of the primary cycloadducts. Efficient syntheses of both 2- and 3-nitroindoles from indole are reported, and the first generation and successful electrophilic trapping of a 2,3-dilithioindole has been achieved.

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14

Xie, Ying, Tengfei Chen, Shaomin Fu, Xing-Shu Li, Yuanfu Deng, Huanfeng Jiang, and Wei Zeng. "Pd-Catalyzed [3+2] cycloaddition of ketoimines with alkynes via directed sp3 C–H bond activation." Chem. Commun. 50, no. 73 (2014): 10699–702. http://dx.doi.org/10.1039/c4cc04676e.

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15

Wang, Hai-Ying, Ming Bao, Bo Jiang, and Liang Li. "Base-mediated isocyanide-based three-component reactions: divergent synthesis of spiro-substituted furans and pyrroles." RSC Advances 6, no. 8 (2016): 6459–66. http://dx.doi.org/10.1039/c5ra25408f.

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A facile base-mediated isocyanide-based three-component cycloaddition protocol for the chemoselective preparation of functionalized spiro-substituted furans and pyrroles derivatives has been designed.

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16

Salehi, Parvin, Zahra Tanbakouchian, Noushin Farajinia-Lehi, and Morteza Shiri. "Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides." RSC Advances 11, no. 22 (2021): 13292–96. http://dx.doi.org/10.1039/d0ra10451e.

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An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles.

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17

Zhou, Ming-Bo, Rui Pi, Fan Teng, Yang Li, and Jin-Heng Li. "Ring-opening formal hetero-[5+2] cycloaddition of 1-tosyl-2,3-dihydro-1H-pyrroles with terminal alkynes: entry to 1-tosyl-2,3-dihydro 2,3-dihydro-1H-azepines." Chemical Communications 55, no. 75 (2019): 11295–98. http://dx.doi.org/10.1039/c9cc05082e.

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18

Ito, S., Y. Tokimaru, and K. Nozaki. "Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons." Chemical Communications 51, no. 1 (2015): 221–24. http://dx.doi.org/10.1039/c4cc06643j.

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The synthesis of the novel azomethine ylide, isoquinolino[4,3,2-de]phenanthridine, and its use in 1,3-dipolar cycloaddition with various alkenes and alkynes to form the corresponding fused pyrrolidines and pyrroles is reported.

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19

Boudriga, Sarra, Mohiedinne Askri, Mohamed Rammah, and Karin Monnier-Jobé. "Reaction of 2-Benzoyl-1,2-Dihydroisoquinoline-1-Carbonitrile Tetrafluoroborate Salt with 2-Arylmethylene-1,3-Indanediones. Regio- and Stereochemistry of the Reaction. Formation of Spiro Compounds." Journal of Chemical Research 2003, no. 4 (April 2003): 208–10. http://dx.doi.org/10.3184/030823403103173499.

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The regio- and stereochemistry of spiro-adducts derived from [4+2] cycloaddition between the title compounds were deduced by 1H NMR data and the elucidated structure of the tetrasubstituted pyrroles obtained by acidic hydrolysis.

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20

Li, Qing, Chuan-Jin Hou, Yun-Ze Hui, Yan-Jun Liu, Rui-Feng Yang, and Xiang-Ping Hu. "Tridentate P,N,N-ligand promoted copper-catalyzed [3 + 2] cycloaddition of propargylic esters with β-enamino esters: synthesis of highly functionalized pyrroles." RSC Advances 5, no. 104 (2015): 85879–83. http://dx.doi.org/10.1039/c5ra19304d.

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By employment of a newly developed tridentate P,N,N-ligand, a copper-catalyzed [3 + 2] cycloaddition of propargylic esters with β-enamino esters for the construction of highly functionalized pyrroles has been developed.

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21

Wang, Kai-Kai, Yan-Xin Xie, Yan-Li Li, Rongxiang Chen, and Zhan-Yong Wang. "Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides." RSC Advances 10, no. 48 (2020): 28720–24. http://dx.doi.org/10.1039/d0ra05687a.

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A simple and efficient method for the synthesis of benzo[4,5]thieno[2,3-c]pyrroles via dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides have been developed.

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22

Prasad, Pulaganti Vijaya, Medi Shanker, Avudoddi Venkanna, Marapala Kumara Swamy, K. Gopichand, and Pallapothula Venkateswar Rao. "Synthesis of functionalized pyrroles and fused pyrroles through intermolecular [3 + 2] cycloaddition reaction." Synthetic Communications 48, no. 9 (March 27, 2018): 1040–44. http://dx.doi.org/10.1080/00397911.2018.1433301.

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23

Gerster, Holger, and Gerhard Maas. "Diverse Reactivities of Acetylenic Iminium Salts Toward 1,3-Oxazolium-5-olates (Münchnones)." Zeitschrift für Naturforschung B 63, no. 4 (April 1, 2008): 384–94. http://dx.doi.org/10.1515/znb-2008-0405.

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AbstractThe acetylenic iminium salts [(c-C3H5)C≡C-C(Ar)=N+Me2]OTf, Ar = phenyl (1a) or 2- thienyl (1b), both react in different ways with three mesoionic münchnones, namely 3-methyl-1,3-oxazolium-5-olate (2), 3-methyl-2-phenyl-1,3-oxazolium-5-olate (6) and 3-methyl-2-phenyl-4- trifluoroacetyl-1,3-oxazolium-5-olate (9). With 2, a [3+2] cycloaddition reaction followed by extrusion of CO2 yields pyrroles 5a, b. In the case of 6, the new münchnones 7a, b are obtained which result from an electrophilic substitution at C-4 by the acetylenic iminium cation. In contrast to 1a, b, the 4,4-but-2-yne 1-iminium salt 1c reacts with münchnone 6 to form pyrrole 8. Finally, the reaction of 1a, b and 9 affords (6-oxo-6H-pyran-3-yl)methylene iminium salts 10a, b under microwave heating conditions. The structures of pyrrole 5a, münchnone 7a, and trifluoromethyl-substituted pyranone 10a were established by single-crystal X-ray diffraction analysis.

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24

Koçak, Ramazan, and Arif Daştan. "Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles." Beilstein Journal of Organic Chemistry 17 (March 15, 2021): 719–29. http://dx.doi.org/10.3762/bjoc.17.61.

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The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels–Alder reaction of tetrazines with p-quinone dibenzosuberenone. Then these pyridazines were converted to the corresponding pyrroles by reductive treatment with zinc. It was observed that all the dihydropyridazines obtained gave absorbance and emission at long wavelengths.

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25

Chen, Xiu-Yu, Hui Zheng, Ying Han, Jing Sun, and Chao-Guo Yan. "The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition." Beilstein Journal of Organic Chemistry 19 (June 29, 2023): 982–90. http://dx.doi.org/10.3762/bjoc.19.73.

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The three-component reaction of isoquinolines, dialkyl acetylenedicarboxylates, and 5,6-unsubstituted 1,4-dihydropyridines in acetonitrile at room temperature afforded functionalized isoquinolino[1,2-f][1,6]naphthyridines in good yields and with high diastereoselectivity. More importantly, the formal [2 + 2] cycloaddition reaction of dialkyl acetylenedicarboxylates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile gave unique 2-azabicyclo[4.2.0]octa-3,7-dienes as major products and 1,3a,4,6a-tetrahydrocyclopenta[b]pyrroles as minor products via further rearrangement.

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26

Sleziak, Robert, and Alzbeta Krutosikova. "ChemInform Abstract: Cycloaddition Reactions of Furo[2,3-b]pyrroles." ChemInform 30, no. 31 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199931048.

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27

Rastogi, Namrata, Lalita Devi, Poornima Mishra, and Ayushi Pokhriyal. "Organo-photocatalytic Synthesis of Functionalized Pyrroles from 2H-Azirines and α-Substituted Nitroalkenes." SynOpen 06, no. 03 (August 23, 2022): 198–207. http://dx.doi.org/10.1055/s-0042-1751360.

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AbstractAn efficient organo-photocatalytic method for the synthesis of tetrasubstituted pyrroles bearing a ketone, ester, alcohol, or nitro group at the 3-position has been developed. The reaction involves visible-light-mediated formal [3+2] dipolar cycloaddition between 2H-azirines and α-substituted nitroalkenes followed by a denitration or debromination sequence. The notable features of the protocol are excellent regioselectivity, wide substrate scope, and high yields of the products.

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28

Kalmode, Hanuman P., Kamlesh S. Vadagaonkar, Kaliyappan Murugan, and Atul C. Chaskar. "A multicomponent pathway-inspired regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles via [3+2] cycloaddition reaction." New Journal of Chemistry 39, no. 6 (2015): 4631–39. http://dx.doi.org/10.1039/c5nj00302d.

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29

Shibata, Miki, Ryuichi Fuchigami, Ryota Kotaka, Kosuke Namba, and Keiji Tanino. "Acid-catalyzed [4+3] cycloaddition reaction of N-nosyl pyrroles." Tetrahedron 71, no. 26-27 (July 2015): 4495–99. http://dx.doi.org/10.1016/j.tet.2015.02.071.

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30

Moiseev, S. V., and N. V. Vasil'ev. "Synthesis and cycloaddition of N-substituted pyrroles with polyfluorinated substituents." Russian Chemical Bulletin 54, no. 8 (August 2005): 1948–53. http://dx.doi.org/10.1007/s11172-006-0063-z.

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31

Markitanov, Yuriy N., Vadim M. Timoshenko, Eduard B. Rusanov, and Yuriy G. Shermolovich. "[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines." Chemistry of Heterocyclic Compounds 57, no. 3 (March 2021): 253–60. http://dx.doi.org/10.1007/s10593-021-02901-x.

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32

Wang, Zhen-Hua, Tong Zhang, Li-Wen Shen, Xiu Yang, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, and Wei-Cheng Yuan. "Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins." Molecules 28, no. 11 (May 29, 2023): 4410. http://dx.doi.org/10.3390/molecules28114410.

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[3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also carried out to verify the practicability of the methodology.

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33

Jones, Raymond C. F., Kevin J. Howard, John R. Nichols, and John S. Snaith. "Annulation of dihydroimidazoles: a 1,3-dipolar cycloaddition route to pyrrolo[1,2-a]imidazoles, pyrrolidines and pyrroles." Journal of the Chemical Society, Perkin Transactions 1, no. 13 (1998): 2061–72. http://dx.doi.org/10.1039/a802048e.

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34

Fuchigami, Ryuichi, Kosuke Namba, and Keiji Tanino. "Concise [4+3] cycloaddition reaction of pyrroles leading to tropinone derivatives." Tetrahedron Letters 53, no. 43 (October 2012): 5725–28. http://dx.doi.org/10.1016/j.tetlet.2012.07.130.

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35

Eddaif, A., S. Kitane, M. Soufiaoui, and P. Mison. "Cycloaddition dipolaire −1,3 sur des 2H-pyrroles: synthèse de quelques dérivés de pyrazolino- et isoxazolino- [5,6-e] pyrroles." Tetrahedron Letters 32, no. 30 (July 1991): 3709–10. http://dx.doi.org/10.1016/s0040-4039(00)79774-7.

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36

Galeev, Andrew R., Anna A. Moroz, Maksim V. Dmitriev, and Andrey N. Maslivets. "Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-b][1,3]oxazine-pyrroles and related products." RSC Advances 12, no. 1 (2022): 578–87. http://dx.doi.org/10.1039/d1ra08384h.

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Rapid epimerization of cycloadducts from Huisgen 1,4-dipoles has been investigated through the synthesis of new spiropyrido[2,1-b][1,3]oxazine-pyrroles and repetition of syntheses from the literature.

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37

Kim, Ikyon, Hee-Kyung Na, Kyung Kim, Sun Kim, and Ge Lee. "A Novel [3+2] Dipolar Cycloaddition Approach to Hexahydrobenzofuro[3,2-b]pyrroles." Synlett 2008, no. 13 (July 15, 2008): 2069–71. http://dx.doi.org/10.1055/s-2008-1077951.

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Kim, Yongju, Jonghoon Kim, and Seung Bum Park. "Regioselective Synthesis of Tetrasubstituted Pyrroles by 1,3-Dipolar Cycloaddition and Spontaneous Decarboxylation." Organic Letters 11, no. 1 (January 2009): 17–20. http://dx.doi.org/10.1021/ol8022193.

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Cox, Joshua B., and John L. Wood. "Synthetic studies toward longeracemine: The intramolecular [4+2] cycloaddition of 3H-pyrroles." Tetrahedron 74, no. 35 (August 2018): 4539–49. http://dx.doi.org/10.1016/j.tet.2018.07.024.

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40

Shibata, Miki, Ryuichi Fuchigami, Ryota Kotaka, Kosuke Namba, and Keiji Tanino. "ChemInform Abstract: Acid-Catalyzed [4 + 3] Cycloaddition Reaction of N-Nosyl Pyrroles." ChemInform 46, no. 42 (October 2015): no. http://dx.doi.org/10.1002/chin.201542132.

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41

Ivan, Beatrice-Cristina, Stefania-Felicia Barbuceanu, Camelia Mia Hotnog, Adriana Iuliana Anghel, Robert Viorel Ancuceanu, Mirela Antonela Mihaila, Lorelei Irina Brasoveanu, et al. "New Pyrrole Derivatives as Promising Biological Agents: Design, Synthesis, Characterization, In Silico, and Cytotoxicity Evaluation." International Journal of Molecular Sciences 23, no. 16 (August 9, 2022): 8854. http://dx.doi.org/10.3390/ijms23168854.

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Abstract:

The current study describes the synthesis, physicochemical characterization and cytotoxicity evaluation of a new series of pyrrole derivatives in order to identify new bioactive molecules. The new pyrroles were obtained by reaction of benzimidazolium bromide derivatives with asymmetrical acetylenes in 1,2-epoxybutane under reflux through the Huisgen [3 + 2] cycloaddition of several ylide intermediates to the corresponding dipolarophiles. The intermediates salts were obtained from corresponding benzimidazole with bromoacetonitrile. The structures of the newly synthesized compounds were confirmed by elemental analysis, spectral techniques (i.e., IR, 1H-NMR and 13C-NMR) and single-crystal X-ray analysis. The cytotoxicity of the synthesized compounds was evaluated on plant cells (i.e., Triticum aestivum L.) and animal cells using aquatic crustaceans (i.e., Artemia franciscana Kellogg and Daphnia magna Straus). The potential antitumor activity of several of the pyrrole derivatives was studied by performing in vitro cytotoxicity assays on human adenocarcinoma-derived cell lines (i.e., LoVo (colon), MCF-7 (breast), and SK-OV-3 (ovary)) and normal human umbilical vein endothelial cells (HUVECs). The obtained results of the cytotoxicity assessment indicated that the tested compounds had nontoxic activity on Triticum aestivum L., while on Artemia franciscana Kellogg nauplii, only compounds 2c and 4c had moderate toxicity. On Daphnia magna, 4b and 4c showed high toxicity; 2a, 2b, and 2c moderate to high toxicity; only 4a and 4d were nontoxic. The compound-mediated cytotoxicity assays showed that several pyrrole compounds demonstrated dose- and time-dependent cytotoxic activity against all tested tumor cell lines, the highest antitumor properties being achieved by 4a and its homologue 4d, especially against LoVo colon cells.

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EDDAIF, A., S. KITANE, M. SOUFIAOUI, and P. MISON. "ChemInform Abstract: 1,3-Dipolar Cycloaddition Reaction with 2H-Pyrroles: Synthesis of Some Pyrazolino- and Isoxazolino(5,6-e)pyrrole Derivatives." ChemInform 23, no. 18 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199218076.

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JONES, R. C. F., K. J. HOWARD, J. R. NICHOLS, and J. S. SNAITH. "ChemInform Abstract: Annulation of Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Pyrrolo[1,2-a]imidazoles, Pyrrolidines and Pyrroles." ChemInform 29, no. 49 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199849147.

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Zhu, Guodong, Shiqi Wu, Xiaoze Bao, Longchen Cui, Yanpeng Zhang, Jingping Qu, Hongbo Chen, and Baomin Wang. "Asymmetric [3+2] cycloaddition of 3-amino oxindole-based azomethine ylides with α,β-ynones: a straightforward approach to spirooxindoles incorporating 2,5-dihydropyrroles and pyrroles." Chemical Communications 53, no. 34 (2017): 4714–17. http://dx.doi.org/10.1039/c7cc01653k.

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Lin, Zhang-qi, Chao-dong Li, Jun-yi Su, Wen-jie Niu, Jian-rong Gao, and Yu-jin Li. "Sequential Cu(II)-promoted oxidation/[3 + 2] cycloaddition/aromatization tandem reaction for the synthesis of 2-substituted benzo[f]isoindole-4,9-dione." Canadian Journal of Chemistry 98, no. 11 (November 2020): 690–96. http://dx.doi.org/10.1139/cjc-2019-0108.

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Abstract:

An efficient method for the synthesis of 2-substituted benzo[f]isoindole-4,9-dione derivatives from N-substituted iminodiacetates and quinones via a Cu(II)-promoted oxidation/[3 + 2] cycloaddition/aromatization tandem reaction was reported. This tandem reaction uses a wide range of N-substituted iminodiacetate derivatives that contain the chain-alkyl, cycloalkyl, and aryl group on the N-atom. Based on optimized reaction conditions, the desired product of 2-substituted benzo[f]isoindole-4,9-diones was obtained in moderate to excellent yields. Taken together, the promising results of this research would provide an especially efficient strategy to synthesize polysubstituted pyrroles from easy available starting materials and promoted by cheaper Cu(OAc)2.

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Efremova, Mariia M., Alexander S. Novikov, Rafael R. Kostikov, Taras L. Panikorovsky, Andrey V. Ivanov, and Alexander P. Molchanov. "Regio- and diastereoselectivity of the cycloaddition of nitrones with N-propadienylindole and pyrroles." Tetrahedron 74, no. 1 (January 2018): 174–83. http://dx.doi.org/10.1016/j.tet.2017.11.056.

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Jones, Raymond C. F., John R. Nichols, and Michael T. Cox. "Annulation of imidazolines: A 1,3-dipolar cycloaddition route to pyrroloimidazoles, pyrrolidines and pyrroles." Tetrahedron Letters 31, no. 16 (January 1990): 2333–36. http://dx.doi.org/10.1016/0040-4039(90)80221-7.

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Wang, Zheng, Ying Shi, Xiaoyan Luo, De-Man Han, and Wei-Ping Deng. "Direct synthesis of pyrroles via 1,3-dipolar cycloaddition of azomethine ylides with ynones." New Journal of Chemistry 37, no. 6 (2013): 1742. http://dx.doi.org/10.1039/c3nj00067b.

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Jursic, Branko S. "Cycloaddition extrusion reactions in the preparation of pyrroles. A DFT-AM1 theoretical study." Journal of Molecular Structure: THEOCHEM 365, no. 1 (June 1996): 55–61. http://dx.doi.org/10.1016/0166-1280(95)04468-x.

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Liu, Jianquan, Zhongxue Fang, Qian Zhang, Qun Liu, and Xihe Bi. "Silver-Catalyzed Isocyanide-Alkyne Cycloaddition: A General and Practical Method to Oligosubstituted Pyrroles." Angewandte Chemie 125, no. 27 (May 6, 2013): 7091–95. http://dx.doi.org/10.1002/ange.201302024.

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