Domino Staudinger/aza-Wittig/Mannich Reaction: An Approach to Diversity of Di- and Tetrahydropyrrole Scaffolds

Anna S Pavlova; Olga A Ivanova; Alexey O Chagarovskiy; Nikolay S Stebunov; Nikolay V Orlov; Alexey N Shumsky; Ekaterina M Budynina; Victor B Rybakov; Igor V Trushkov

doi:10.1002/chem.201604056

Domino Staudinger/aza-Wittig/Mannich Reaction: An Approach to Diversity of Di- and Tetrahydropyrrole Scaffolds

Chemistry. 2016 Dec 12;22(50):17967-17971. doi: 10.1002/chem.201604056. Epub 2016 Oct 31.

Authors

Affiliations

¹ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation.
² Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology n.a. Dmitriy Rogachev, Samory Mashela st., 1, Moscow, 117997, Russian Federation.
³ Faculty of Science, Russian University of People's Friendship, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation.
⁴ Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation.
⁵ Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina 4, Moscow, 119334, Russian Federation.

PMID: 27685760
DOI: 10.1002/chem.201604056

Abstract

A highly efficient and selective domino reaction producing valuable di- and tetrahydropyrrole-based skeletons from azidoethyl-substituted CH-acids and (thio)carbonyl compounds has been developed. By involving the additional functional groups in starting compounds into the domino reaction or postmodification of the primary reaction products, the simple construction of the pharmaceutically relevant three- and polycyclic azaheterocyclic scaffolds was demonstrated.

Keywords: azides; domino reactions; donor-acceptor cyclopropanes; nitrogen heterocycles; synthesis design.