Unique Pseudo-Cross-Conjugated Mesomeric Betaines via an Iodate-Promoted Reaction of 3,3-Difluorocyclopropenes, Pyridines, and Anilines

Unique Pseudo-Cross-Conjugated Mesomeric Betaines via an Iodate-Promoted Reaction of 3,3-Difluorocyclopropenes, Pyridines, and Anilines Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2021, Volume: 87, Number: 1, Pages: 652-669 Pages count : 18 DOI: 10.1021/acs.joc.1c02630

Authors

Nechaev Ilya V. ^1,2 , Cherkaev Georgij V. ³ , Sheremetev Aleksei B. ²

Affiliations

1	Asinex LTD, 20 Geroev Panfilovtsev Street, 125480 Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russia
3	Enikolopov Institute of Synthetic Polymeric Materials, Russian Academy of Sciences, 70 Profsoyuznaya Street, 117393 Moscow, Russia

A simple method for the synthesis of (E)-3-arylimino-3H-indolizin-4-ium-1-olates by an iodate-promoted multicomponent reaction between 3,3-difluorocyclopropenes, pyridines, and anilines was discovered. The reaction products belong to a limited and underexplored class of pseudo-cross-conjugated heterocyclic mesomeric betaines isoconjugated with odd nonalternant hydrocarbon anions, whose properties were studied. Reversible nucleophilic addition at the C5 position was revealed as their main chemical feature, which had an access to novel fully conjugated 1,5-dioxo-3-arylamino-1,5-dihydroindolizine and tetracyclic 4-oxo-4,6-dihydrocyclopenta[4,5]pyrimido[2,1,6-cd]indolizine ring systems in one step. Both the synthesis of betaines and their transformations demonstrate a high level of functional group compatibility, allowing the ready preparation of a number of structurally attractive compounds for materials or medicinal chemistry.

Nechaev I.V. , Cherkaev G.V. , Sheremetev A.B.
Unique Pseudo-Cross-Conjugated Mesomeric Betaines via an Iodate-Promoted Reaction of 3,3-Difluorocyclopropenes, Pyridines, and Anilines
Journal of Organic Chemistry. 2021. V.87. N1. P.652-669. DOI: 10.1021/acs.joc.1c02630 WOS Scopus OpenAlex

≡ Web of science:	WOS:000735997600001
≡ Scopus:	2-s2.0-85122011395
≡ OpenAlex:	W4200202562