Peri-Annulated Indoles from Donor–Acceptor Cyclopropanes: Synthesis of 5,6-Dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles

Peri-Annulated Indoles from Donor–Acceptor Cyclopropanes: Synthesis of 5,6-Dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles Full article

Journal

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

Output data

Year: 2025, Volume: 90, Number: 25, Pages: 8754–8766 Pages count : DOI: 10.1021/acs.joc.5c00928

Authors

Antropov Sergey M. ¹ , Tokmacheva Sofiya A. ^2,1 , Levina Irina I. ³ , Ivanova Olga A. ⁴ , Trushkov Igor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia
2	Higher Chemical College of RAS, Mendeleev University of Chemical Technology, Miusskaya sq. 9-1, Moscow 125047, Russia
3	Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina 4, Moscow 119334, Russia
4	Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow 119991, Russia

A method for one-step conversion of (3-formylindol-4-yl)-substituted donor–acceptor cyclopropanes to 5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles has been developed. The scope and limitations of this reaction, as well as the Lewis acid effect on the process chemoselectivity, have been determined. Straightforward transformations of the obtained products provide direct access to alkaloid-like tetracyclic compounds.

Antropov S.M. , Tokmacheva S.A. , Levina I.I. , Ivanova O.A. , Trushkov I.V.
Peri-Annulated Indoles from Donor–Acceptor Cyclopropanes: Synthesis of 5,6-Dihydro-1H-[1,2]diazepino[4,5,6-cd]indoles
Journal of Organic Chemistry. 2025. V.90. N25. P.8754–8766. DOI: 10.1021/acs.joc.5c00928 WOS Scopus OpenAlex

Web of science:	WOS:001510199600001
Scopus:	2-s2.0-105008276012
OpenAlex:	W4411241654

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