(3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines

Alexey O Chagarovskiy; Vladimir S Vasin; Vladimir V Kuznetsov; Olga A Ivanova; Victor B Rybakov; Alexey N Shumsky; Nina N Makhova; Igor V Trushkov

doi:10.1002/anie.201805258

(3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines

Angew Chem Int Ed Engl. 2018 Aug 6;57(32):10338-10342. doi: 10.1002/anie.201805258. Epub 2018 Jul 17.

Authors

Alexey O Chagarovskiy¹, Vladimir S Vasin¹, Vladimir V Kuznetsov², Olga A Ivanova³, Victor B Rybakov³, Alexey N Shumsky⁴, Nina N Makhova², Igor V Trushkov^{1

5}

Affiliations

¹ Dmitry Rogachev National Research Center of, Pediatric Hematology, Oncology and Immunology, Samory Mashela, 1, Moscow, 117997, Russian Federation.
² N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation.
³ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation.
⁴ Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina 4, Moscow, 119334, Russian Federation.
⁵ Faculty of Science, RUDN University, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation.

PMID: 29936708
DOI: 10.1002/anie.201805258

Abstract

The first example of (3+3)-annulation of two different three-membered rings is reported herein. Donor-acceptor cyclopropanes in reaction with diaziridines were found to afford perhydropyridazine derivatives in high yields and diastereoselectivity under mild Lewis acid catalysis. The disclosed reaction is applicable for the broad substrate scope and exhibits an excellent functional group tolerance.

Keywords: annulation; diaziridines; donor-acceptor cyclopropanes; nitrogen heterocycles; small ring systems.