Communications

Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence

O. V. Petrova, I. A. Ushakov, B. A. Trofimov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russian Federation

Аннотация: 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) cyclizes with α,β-ynones under catalyst-free conditions (MeCN, 3 h) to give a mixture of isolable diverse fused heterocycles including [3 + 3]- and [4 + 2]-cycloadducts as well as DBU ring expansion products, 14- and 15-membered heterocyclic systems incorporating the pyridinone moiety, in 48–58% total yield. Some of the synthesized cycloadducts exhibit blue-green fluorescence with large Stokes shift.

Ключевые слова: 1,8-diazabicyclo[5.4.0]undec-7-ene, ynones, fused heterocyclic system, DBU ring expansion, [3 + 3]- and [4 + 2]-cycloadducts.

Поступила в редакцию: 01.07.2025
Принята в печать: 19.09.2025

Язык публикации: английский

DOI: 10.71267/mencom.7865