Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Eugene V Babaev; Ivan A Shadrin

doi:10.3390/molecules26072050

Indolizines and Their Hetero/Benzo Derivatives in Reactions of [8+2] Cycloaddition

Molecules. 2021 Apr 3;26(7):2050. doi: 10.3390/molecules26072050.

Authors

Eugene V Babaev^{1

2

3}, Ivan A Shadrin¹

Affiliations

¹ Chemistry Department, Moscow State University, Leninskie Gory, 1 Str. 3, 119899 Moscow, Russia.
² Higher School of Economics, National Research University, 7 Vavilova Str., 117312 Moscow, Russia.
³ N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russia.

Abstract

Peculiarities of [8+2] cycloaddition of acetylenes to indolizines are reviewed. Especially mentioned are indolizines with leaving groups at positions 3 and 5. Cycloaddition to aza- and benzo derivatives are reviewed, as well as 1,10-cyclizations and processes leading to cyclazines where indolizines are intermediates. Mechanistic features (adducts and cycloadducts) and theoretical aspects (one- or two-steps mechanism) are reviewed.

Keywords: 1,10-cyclizations; [8+2] cycloaddition; azaindolizines; benzoindolizines; catalysts; cyclazine; indolizine; mechanism.

Publication types

Review