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Journal articles on the topic 'Annulation reactions'

Author: Grafiati

Published: 6 September 2023

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1

Fang, Lei, Alexander Kalin, and Jongbok Lee. "Annulation Reactions for Conjugated Ladder-Type Oligomers." Synlett 29, no. 08 (February 27, 2018): 993–98. http://dx.doi.org/10.1055/s-0036-1591945.

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Conjugated ladder-type oligomers are a class of important functional organic materials. They possess intriguing properties stemming from their fully fused aromatic backbones. The construction of the ladder-type backbone relies on a ‘ladderization’ step, which may be accomplished through either kinetically or thermodynamically controlled annulation reactions. The attributes of these reactions are discussed, with relevant recent examples. The development of these reactions is key to continued advances and innovation in the field of organic conjugated materials.1 Introduction2 Kinetic Annulations3 Thermodynamic Annulations4 Future Outlooks and Conclusion

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2

Song, Ren-Jie, Bin Wei, Ke-Wei Li, Yan-Chen Wu, and Shi-Qi Tong. "Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review." Synthesis 52, no. 24 (June 8, 2020): 3855–65. http://dx.doi.org/10.1055/s-0040-1707835.

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The γ-lactone skeleton is very important component of various natural products, biological molecules, food additives, and perfumes. As a result, much effort has been made towards such compounds. In this review, we summarize recent progress in transition-metal-catalyzed annulation reactions for the formation of γ-lactone derivatives through a radical pathway. Various reagents, such as anhydrides, Togni’s reagent, TMSN3, arenesulfonyl chlorides, arenediazonium salts, dibenzoyl peroxides, O-benzoylhydroxylamine, NFSI, and α-halocarboxylic compounds, used in radical cyclization reactions are described, and the mechanisms of these radical annulation reactions are also discussed.1 Introduction2 Annulations of Alkenes with Anhydrides3 Annulations of Unsaturated Carboxylic Acids with Nucleophiles4 Annulations of Alkenes with α-Halocarboxylic Compounds5 Conclusions and Outlook

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3

Comesse, Sébastien, Ismail Alahyen, Laure Benhamou, Vincent Dalla, and Catherine Taillier. "20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions." Synthesis 53, no. 19 (May 10, 2021): 3409–39. http://dx.doi.org/10.1055/a-1503-7932.

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AbstractAcrylamides are versatile building blocks that are easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proven to be efficient domino partners, leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal-free and metal-triggered reactions followed by an annulation will be presented; these two approaches allow good modulation of the reactivity of the polyvalent acrylamides.1 Introduction2 Metal-Free Annulations2.1 Domino Reactions Triggered by a Michael Addition2.2 Domino Reactions Triggered by an Aza-Michael Addition2.3 Domino Processes Triggered by an Acylation Reaction2.4 Domino Reactions Triggered by a Baylis–Hillman Reaction2.5 Cycloadditions and Domino Reactions2.6 Miscellaneous Domino Reactions3 Metal-Triggered/Mediated Annulations3.1 Zinc-Promoted Transformations3.2 Rhodium-Catalyzed Functionalization/Annulation Cascades3.3 Cobalt-Catalyzed Functionalization/Annulation Cascades3.4 Ruthenium-Catalyzed Functionalization/Annulation Cascades3.5 Iron-Catalyzed Functionalization/Annulation Cascades3.6 Palladium-Catalyzed Functionalization/Annulation Cascades3.7 Copper-Catalyzed Transformations3.8 Transition Metals Acting in Tandem in Domino Processes4 Radical Cascade Reactions5 Conclusion

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4

Gerasyuto, Aleksey I., Zhi-Xiong Ma, Grant S. Buchanan, and Richard P. Hsung. "Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis." Beilstein Journal of Organic Chemistry 9 (June 18, 2013): 1170–78. http://dx.doi.org/10.3762/bjoc.9.131.

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A successful enone version of an intramolecular aza-[3 + 3] annulation reaction is described here. Use of piperidinium trifluoroacetate salt as the catalyst and toluene as the solvent appears to be critical for a successful annulation. We also demonstrated for the first time that microwave irradiation can accelerate aza-[3 + 3] annulation reactions. An attempt to expand the scope of the enone aza-[3 + 3] annulation was made in the form of propyleine synthesis as a proof of concept. While synthesis of the enone annulation precursor was successfully accomplished, the annulation proved to be challenging and was only modestly successful.

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5

Cardoso, Ana L., and Maria I. L. Soares. "1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings." Current Organic Chemistry 23, no. 27 (January 15, 2020): 3064–134. http://dx.doi.org/10.2174/1385272823666191203122959.

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The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation reactions.

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6

Mao, Guoliang, Qiang Huang, and Congyang Wang. "Rhenium-Catalyzed Annulation Reactions." European Journal of Organic Chemistry 2017, no. 25 (May 23, 2017): 3549–64. http://dx.doi.org/10.1002/ejoc.201700285.

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7

Jeganmohan, Masilamani, and Pinki Sihag. "Recent Advances in Transition-Metal-Catalyzed C–H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes." Synthesis 53, no. 18 (June 14, 2021): 3249–62. http://dx.doi.org/10.1055/a-1528-1711.

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AbstractBicyclic alkenes, including oxa- and azabicyclic alkenes, readily undergo activation with facial selectivity in the presence of transition-metal complexes. This is due to the intrinsic angle strain on the carbon–carbon double bonds in such unsymmetrical bicyclic systems. During the past decades considerable progress has been made in the area of ring opening of bicyclic strained rings by employing the concept of C–H activation. This short review comprehensively compiles the various C–H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydroarylation, and annulation reactions.1 Introduction2 Reactions of Heterobicyclic Ring Systems2.1 Ring-Opening Reactions of Oxa- and Azabenzonorbornadienes2.1.1 Reactions Using 7-Oxabenzonorbornadienes2.1.2 Reactions Using 7-Azabenzonorbornadienes2.2 Hydroarylation Reactions2.3 Annulation Reactions2.4 Other Reactions3 Conclusion

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8

Li, Yangyan, Xiang Chen, Xiaoming Chen, and Xiao Shen. "Organophosphine-Catalyzed [4C+X] Annulations." Molecules 23, no. 11 (November 19, 2018): 3022. http://dx.doi.org/10.3390/molecules23113022.

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In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize the remarkable progress, emphasizing reaction mechanisms and key intermediates involved in the processes. The discussion is classified according to the type of electrophilic reactants that acted as C4 synthons in the annulation process, in the order of α-alkyl allenoates, γ-alkyl allenoates, α-methyl allene ketones, β′-OAc allenoate, δ-OAc allenoate, activated dienes and cyclobutenones.

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9

Dillon, John L., Qi Gao, Elizabeth A. Dillon, and Nick Adams. "New annulation reactions of cyclobutenones." Tetrahedron Letters 38, no. 13 (March 1997): 2231–34. http://dx.doi.org/10.1016/s0040-4039(97)00331-6.

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10

Qian, Hui, Wanxiang Zhao, and Jianwei Sun. "Siloxy Alkynes in Annulation Reactions." Chemical Record 14, no. 6 (August 29, 2014): 1070–85. http://dx.doi.org/10.1002/tcr.201402042.

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11

Dyker, Gerald. "Transition metal catalyzed annulation reactions. Part 3. Palladium-catalyzed annulation reactions of 1,8-diiodonaphthalene." Journal of Organic Chemistry 58, no. 1 (January 1993): 234–38. http://dx.doi.org/10.1021/jo00053a042.

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12

Wang, Nengzhong, Zugen Wu, Junjie Wang, Nisar Ullah, and Yixin Lu. "Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis." Chemical Society Reviews 50, no. 17 (2021): 9766–93. http://dx.doi.org/10.1039/d0cs01124j.

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A comprehensive and updated summary of asymmetric organocatalytic annulation reactions is presented; in particular, the applications of these annulation strategies to natural products synthesis are highlighted.

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13

Shin, Seunghoon. "The effect of acceptor-substituted alkynes in gold-catalyzed intermolecular reactions." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 373–79. http://dx.doi.org/10.1515/pac-2014-5039.

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Abstract Alkynes substituted with electron-withdrawing groups participated in various intermolecular reactions with olefin substrates, including [4 + 2] annulation of propiolic acids, intermolecular metathesis-type reaction and carboalkoxylation involving allylethers.

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14

Gholamhosseyni, Maral, and Ebrahim Kianmehr. "A ruthenium-catalyzed alkenylation–annulation approach for the synthesis of indazole derivatives via C–H bond activation." Organic & Biomolecular Chemistry 16, no. 33 (2018): 5973–78. http://dx.doi.org/10.1039/c8ob00999f.

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15

Liu, Honglei, Yan Lin, Yan Zhao, Miaoren Xiao, Leijie Zhou, Qijun Wang, Cheng Zhang, Dongqi Wang, Ohyun Kwon, and Hongchao Guo. "Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways." RSC Advances 9, no. 3 (2019): 1214–21. http://dx.doi.org/10.1039/c8ra09852b.

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16

Curran, Dennis P., and Churl Min Seong. "Radical annulation reactions of allyl iodomalononitriles." Tetrahedron 48, no. 11 (January 1992): 2175–90. http://dx.doi.org/10.1016/s0040-4020(01)88882-7.

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17

Danheiser, Rick L., ]Atsushi Nishida, Selvaraj Savariar, and Michael P. Trova. "Trialkylsilyloxyalkynes: Synthesis and aromatic annulation reactions." Tetrahedron Letters 29, no. 39 (January 1988): 4917–20. http://dx.doi.org/10.1016/s0040-4039(00)80640-1.

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18

Nevill, C. R., and P. L. Fuchs. "Annulation Reactions ofOrtho-Chloromethyl Aryl Cuprates." Synthetic Communications 20, no. 5 (March 1990): 761–72. http://dx.doi.org/10.1080/00397919008052320.

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19

Rajagopal, D., R. Narayanan, and S. Swaminathan. "Enantioselective solvent-free Robinson annulation reactions." Journal of Chemical Sciences 113, no. 3 (June 2001): 197–213. http://dx.doi.org/10.1007/bf02704070.

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20

Mitchell, Anthony S., and Richard A. Russell. "Annulation reactions with stabilized phthalide anions." Tetrahedron 51, no. 18 (May 1995): 5207–36. http://dx.doi.org/10.1016/0040-4020(95)00247-6.

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21

DYKER, G. "ChemInform Abstract: Transition Metal Catalyzed Annulation Reactions. Part 3. Palladium- Catalyzed Annulation Reactions of 1,8-Diiodonaphthalene." ChemInform 24, no. 21 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199321077.

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22

Thakur, Rima, Yogesh Jaiswal, and Amit Kumar. "Imidates: an emerging synthon for N-heterocycles." Organic & Biomolecular Chemistry 17, no. 46 (2019): 9829–43. http://dx.doi.org/10.1039/c9ob01899a.

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This review highlights the recent application of imidates as building blocks for the synthesis of saturated and un-saturated N-heterocycles via C–N annulation reactions under acid/base/metal-catalyzed/radical-mediated reaction conditions.

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23

Potapov, Vladimir A., Roman S. Ishigeev, Lyudmila A. Belovezhets, Irina V. Shkurchenko, and Svetlana V. Amosova. "New Water-Soluble Condensed Heterocyclic Compounds with Antimicrobial Activity Based on Annulation Reactions of 8-Quinolinesulfenyl Halides with Natural Products and Alkenes." Applied Sciences 11, no. 18 (September 14, 2021): 8532. http://dx.doi.org/10.3390/app11188532.

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The annulation reactions of 8-quinolinesulfenyl halides with natural products and alkenes affording new water-soluble [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives in high or quantitative yields are developed in this study. The reactions with styrene derivatives and terminal alkenes including allyl arenes proceed in a regioselective manner but with the opposite regiochemistry. The reactions with terminal alkenes including allyl arenes occur in an anti-Markovnikov fashion (regarding addition of the 8-quinolinesulfenyl electrophile to the double bond) to give 2-organyl-2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium halides, while the reactions with styrene derivatives proceed in a Markovnikov fashion, leading to 3-substituted condensed heterocyclic compounds. In general, styrene derivatives demonstrate higher reactivity in the annulation reactions compared to the terminal alkenes. Antimicrobial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli are evaluated. The compounds with high antimicrobial activity are found. The annulation products of the reactions of 8-quinolinesulfenyl halides with 1H-indene, eugenol, methyl eugenol and 1-heptene, are superior in their activity compared to the antibiotic gentamicin.

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24

Wu, Qiuyue, Zhanhui Yang, and Jiaxi Xu. "Temperature-dependent annuloselectivity and stereochemistry in the reactions of methanesulfonyl sulfene with imines." Organic & Biomolecular Chemistry 14, no. 30 (2016): 7258–67. http://dx.doi.org/10.1039/c6ob01259k.

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The annuloselectivity in the reactions of methanesulfonyl sulfene and imines varies with temperature. At 20 °C, the [2^s+ 2ⁱ] annulation occurs exclusively, while at −78 °C, the [2^s+ 2ⁱ+ 2ⁱ] annulation ofN-methyl imines takes place specifically.

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25

Potapov, Vladimir A., Roman S. Ishigeev, and Svetlana V. Amosova. "Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides." Molecules 26, no. 4 (February 20, 2021): 1116. http://dx.doi.org/10.3390/molecules26041116.

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Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied. The opposite regiochemistry was observed in the reactions with vinyl chalcogenides and tetravinyl silane. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.

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26

Ciesielski, Jennifer, Daniel P. Canterbury, and Alison J. Frontier. "β-Iodoallenolates as Springboards for Annulation Reactions." Organic Letters 11, no. 19 (October 2009): 4374–77. http://dx.doi.org/10.1021/ol901721y.

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27

Yamane, Osamu, Ken-ichi Sugiura, Hitoshi Miyasaka, Kazuya Nakamura, Tatsuhiko Fujimoto, Kazuki Nakamura, Takahiro Kaneda, Yoshiteru Sakata, and Masahiro Yamashita. "Pyrene-Fused Porphyrins: Annulation Reactions ofmeso-Pyrenylporphyrins." Chemistry Letters 33, no. 1 (January 2004): 40–41. http://dx.doi.org/10.1246/cl.2004.40.

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28

DILLON, J. L., Q. GAO, E. A. DILLON, and N. ADAMS. "ChemInform Abstract: New Annulation Reactions of Cyclobutenones." ChemInform 28, no. 30 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199730074.

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29

Qian, Hui, Wanxiang Zhao, and Jianwei Sun. "ChemInform Abstract: Siloxy Alkynes in Annulation Reactions." ChemInform 46, no. 9 (February 16, 2015): no. http://dx.doi.org/10.1002/chin.201509316.

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30

DYKER, G. "ChemInform Abstract: New Palladium-Catalyzed Annulation Reactions." ChemInform 26, no. 6 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199506271.

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31

Liu, Xu-Guang, Yin Wei, and Min Shi. "Probing Phosphane-Mediated [2+1] Annulation Reactions." European Journal of Organic Chemistry 2010, no. 10 (February 18, 2010): 1977–88. http://dx.doi.org/10.1002/ejoc.200901235.

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32

Haito, Akira, and Naoto Chatani. "Rh(i)-Catalyzed [3+2] annulation reactions of cyclopropenones with amides." Chemical Communications 55, no. 40 (2019): 5740–42. http://dx.doi.org/10.1039/c9cc02397f.

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33

Carvalho, M. Fernanda N. N., Armando J. L. Pombeiro, Gabriele Wagner, Bjørn Pedersen, and Rudolf Herrmann. "Cascade Reaction of Camphor-Derived Diynes with Transition Metal Compounds." Zeitschrift für Naturforschung B 54, no. 6 (June 1, 1999): 725–33. http://dx.doi.org/10.1515/znb-1999-0604.

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Platinum(II) catalyzes the isomerization of camphor sulfonamide diynes in a cascade reaction involving annulation of a five-membered ring to the camphor skeleton, ring-enlargement by C-C bond cleavage, reduction of sulfur(VI) to sulfur(IV), and oxidation of a hydroxy group to a ketone. The reactions of the diynes with other transition metal compounds were also studied. Copper, gold and rhenium give final products similar to those obtained with simple Brønsted acids or halogens, mainly by annulation o f a five-membered ring to the camphor moiety, accompanied by reduction of a sulfonamide to a sulfinamide group, but lacking the ring-enlargement step. Palladium(II) occupies an intermediate position as both types o f products are obtained. The reaction mechanism and intermediates are discussed

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34

Liu, Yi, Puying Luo, Yang Fu, Tianxin Hao, Xuan Liu, Qiuping Ding, and Yiyuan Peng. "Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives." Beilstein Journal of Organic Chemistry 17 (September 22, 2021): 2462–76. http://dx.doi.org/10.3762/bjoc.17.163.

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Great progress has been made in the tandem annulation of enynes in the past few years. This review only presents the corresponding reactions of 1,3-enyne structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly introduce the applications of the products and the reaction mechanisms for the synthesis of corresponding N-heterocycles.

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35

de Nanteuil, F., F. De Simone, R. Frei, F. Benfatti, E. Serrano, and J. Waser. "Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes." Chem. Commun. 50, no. 75 (2014): 10912–28. http://dx.doi.org/10.1039/c4cc03194f.

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36

Zhou, Tao, Bin Li, and Baiquan Wang. "Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes: a facile access to substituted and fused carbazoles." Chemical Communications 53, no. 47 (2017): 6343–46. http://dx.doi.org/10.1039/c7cc02808c.

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Rhodium-catalyzed C2 and C4 C–H activation/annulation of 3-(1H-indol-3-yl)-3-oxopropanenitriles with internal alkynes has been developed. Substituted and fused carbazole derivatives were obtained through formal rhodium-catalyzed (4+2) or tandem (4+2) and (5+2) cycloaddition reactions under mild reaction conditions in good yields.

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37

Bao, Xiazhen, Wei Jiang, Jia Liang, and Congde Huo. "One-electron oxidative dehydrogenative annulation and cyclization reactions." Organic Chemistry Frontiers 7, no. 15 (2020): 2107–44. http://dx.doi.org/10.1039/d0qo00422g.

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This review focuses on the recent advances in one-electron oxidation involved oxidative dehydrogenative annulations and cyclizations for the intermolecular and intramolecular construction of valuable ring structures.

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38

Liu, Jinying, Xiaolan Fu, Yang Zhou, Guangyuan Zhou, Yongjiu Liang, and Dewen Dong. "A Facile and Divergent Synthesis of Substituted Pyridine-2,4(1H,3H)-diones and 4H-Thiopyran-4-ones from α-Alkenoyl-α-carbamoyl Ketene-S,S-acetals." Australian Journal of Chemistry 63, no. 8 (2010): 1267. http://dx.doi.org/10.1071/ch09489.

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A facile and divergent synthesis of substituted pyridine-2,4(1H,3H)-diones and 4H-thiopyran-4-ones from readily available α-alkenoyl-α-carbamoyl ketene-S,S-acetals has been developed. Subjected to N,N-dimethylformamide at 125°C, α-alkenoyl-α-carbamoyl ketene-S,S-acetals underwent an intramolecular aza-nucleophilic vinyl substitution reaction, a formal [5C + 1N] annulation, to give the corresponding substituted pyridine-2,4(1H,3H)-diones in high yields, whereas in the presence of Na2S·9H2O in DMF at 75°C, tandem intermolecular and intramolecular thia-nucleophilic vinyl substitution reactions, a formal [5C + 1S] annulation, occurred to produce the corresponding substituted 4H-thiopyran-4-ones in good yields.

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39

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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40

Xie, Wucheng, Xin Chen, Junjun Shi, Jieshen Li, and Riyao Liu. "Synthesis of 1-aminoindole derivatives via Rh(iii)-catalyzed annulation reactions of hydrazines with sulfoxonium ylides." Organic Chemistry Frontiers 6, no. 15 (2019): 2662–66. http://dx.doi.org/10.1039/c9qo00524b.

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41

Tang, Dong, Jing Wang, Ping Wu, Xin Guo, Ji-Hui Li, Sen Yang, and Bao-Hua Chen. "Synthesis of 1,2,4-triazine derivatives via [4 + 2] domino annulation reactions in one pot." RSC Advances 6, no. 15 (2016): 12514–18. http://dx.doi.org/10.1039/c5ra26638f.

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42

Kondalarao, Koneti, Somratan Sau, and Akhila K. Sahoo. "Sulfoximine Assisted C–H Activation and Annulation via Vinylene Transfer: Access to Unsubstituted Benzothiazines." Molecules 28, no. 13 (June 27, 2023): 5014. http://dx.doi.org/10.3390/molecules28135014.

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In this study, we report the synthesis of unsubstituted 1,2-benzothiazines through a redox-neutral Rh(III)-catalyzed C–H activation and [4+2]-annulation of S–aryl sulfoximines with vinylene carbonate. Notably, the introduction of an N-protected amino acid ligand significantly enhances the reaction rate. The key aspect of this redox-neutral process is the utilization of vinylene carbonate as an oxidizing acetylene surrogate and an efficient vinylene transfer agent. This vinylene carbonate enables the cyclization with the sulfoximine motifs, successfully forming a diverse array of 1,2-benzothiazine derivatives in moderate to good yields. Importantly, this study highlights the potential of Rh(III)-catalyzed C–H activation and [4+2]-annulation reactions for the synthesis of optically pure 1,2-benzothiazines with high enantiomeric purity.

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Hu, Gaobo, Yun Zhang, Jue Su, Zezhou Li, Yuxing Gao, and Yufen Zhao. "Ag-mediated cascade decarboxylative coupling and annulation: a convenient route to 2-phosphinobenzo[b]phosphole oxides." Organic & Biomolecular Chemistry 13, no. 30 (2015): 8221–31. http://dx.doi.org/10.1039/c5ob00959f.

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Martins, Guilherme M., Geórgia C. Zimmer, Samuel R. Mendes, and Nisar Ahmed. "Electrifying green synthesis: recent advances in electrochemical annulation reactions." Green Chemistry 22, no. 15 (2020): 4849–70. http://dx.doi.org/10.1039/d0gc01324b.

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Liu, Yiyi, and Rong Zhou. "Progress in Annulation Reactions Based on Huisgen Zwitterion." Chinese Journal of Organic Chemistry 39, no. 9 (2019): 2365. http://dx.doi.org/10.6023/cjoc201903041.

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Curran, Dennis P., Meng Hsin Chen, Eric Spletzer, Churl Min Seong, and Chi Tai Chang. "Atom-transfer addition and annulation reactions of iodomalonates." Journal of the American Chemical Society 111, no. 24 (November 1989): 8872–78. http://dx.doi.org/10.1021/ja00206a016.

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Yamamoto, Yoshihiko. "Recent topics of Cp∗RuCl-catalyzed annulation reactions." Tetrahedron Letters 58, no. 40 (October 2017): 3787–94. http://dx.doi.org/10.1016/j.tetlet.2017.08.040.

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Corey, E. J., Wei-guo Su, and Ioannis N. Houpis. "Useful new annulation reactions of vicinal dicarboxylic esters." Tetrahedron Letters 27, no. 49 (January 1986): 5951–54. http://dx.doi.org/10.1016/s0040-4039(00)85370-8.

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Elliott, Mark C., Elbertus Kruiswijk, and Matthew S. Long. "Annulation reactions of azoles and azolines with heterocumulenes." Tetrahedron 57, no. 31 (July 2001): 6651–77. http://dx.doi.org/10.1016/s0040-4020(01)00442-2.

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Kohn, Benjamin L., and Elizabeth R. Jarvo. "Palladium-Catalyzed Annulation Reactions for Diastereoselective Cyclopentene Synthesis." Organic Letters 13, no. 18 (September 16, 2011): 4858–61. http://dx.doi.org/10.1021/ol2019423.

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