Synthesis, Table of Contents Synthesis 2022; 54(17): 3845-3857DOI: 10.1055/a-1742-2005 special topic Special Issue in memory of Prof. Ferenc Fülöp Electrocyclization and Unexpected Reactions of Non-Stabilized α,β:γ,δ-Unsaturated Azomethine Ylides: Experimental and Theoretical Studies István G. Molnár a Servier Research Institute of Medicinal Chemistry, 7 Záhony utca., 1031 Budapest, Hungary , Zoltán Mucsi b Femtonics Research Institute, 59 Tűzoltó utca, 1094 Budapest, Hungary c Institute of Chemistry, Faculty of Materials Science and Engineering, University of Miskolc, 3515 Miskolc, Hungary , Ervin Kovács ∗ b Femtonics Research Institute, 59 Tűzoltó utca, 1094 Budapest, Hungary d Institute of Materials and Environmental Chemistry, Research Centre for Natural Sciences, 2 Magyar tudósok körútja, 1117 Budapest, Hungary , Miklós Nyerges∗ a Servier Research Institute of Medicinal Chemistry, 7 Záhony utca., 1031 Budapest, Hungary › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Versatile, two-step syntheses of dihydrodibenzo[c,e]azepines, carbazole derivatives, and other alkaloid-type drug-like scaffolds by in situ generated azomethine ylide-induced intramolecular electrocyclization reaction from commercially available materials are presented. The reaction mechanisms of transition-metal-free carbon–carbon bond formation and the role of the kinetic control, resulting in the good regioselectivity, were confirmed by theoretical calculations. Key words Key wordsalkaloid - azomethine ylide - dihydro-5H-dibenzo[c,e]azepine - electrocyclization - NICS Full Text References References For reviews on 1,5- and 1,7-electrocyclizations of conjugated 1,3-dipoles, see: 1a Nyerges M, Tóth J, Groundwater PW. Synlett 2008; 1269 1b Pinho e Melo TM. V. D. Eur. J. Org. Chem. 2006; 2873 1c Groundwater PW, Nyerges M. Adv. Heterocycl. Chem. 1999; 73: 97 1d Zecchi G. Synthesis 1991; 181 1e Huisgen R. Angew. Chem., Int. Ed. Engl. 1980; 19: 947 1f Taylor EC, Turchi IJ. Chem. Rev. 1979; 79: 181 2a Shun-ichi N, Yasumasa H, Tetsuhiro N. Tetrahedron Lett. 2018; 59: 760 2b Pompeo MM, Cheah JH, Movassaghi M. J. Am. Chem. Soc. 2019; 141: 14411 2c Chaturvedula PV, Mercer SE, Fang H, Han X, Luo G, Dubowchik GM, Poindexter GS. US Pat. Appl. 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