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

Olga Vital'evna Petrova 1
Olga Vital'evna Petrova
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
10.71267/mencom.7865
Published 2026-02-03
Communication , Volume 36, Issue 2, 171-173
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Petrova O. V., Ushakov I. A., Trofimov B. A. Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 171-173.
GOST all authors (up to 50) Copy
Petrova O. V., Ushakov I. A., Trofimov B. A. Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 171-173.
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TY - JOUR
DO - 10.71267/mencom.7865
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7865
TI - Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence
T2 - Mendeleev Communications
AU - Petrova, Olga Vital'evna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2026
DA - 2026/02/03
PB - Mendeleev Communications
SP - 171-173
IS - 2
VL - 36
ER -
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@article{2026_Petrova,
author = {Olga Vital'evna Petrova and Igor Alekseevich Ushakov and Boris Aleksandrovich Trofimov},
title = {Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7865},
number = {2},
pages = {171--173},
doi = {10.71267/mencom.7865}
}
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Petrova, Olga Vital'evna, et al. “Catalyst-free cyclization of DBU with α,β-ynones: substituent-controlled divergence.” Mendeleev Communications, vol. 36, no. 2, Feb. 2026, pp. 171-173. https://mendcomm.colab.ws/publications/10.71267/mencom.7865.

Keywords

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

Abstract

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.

Funders

Ministry of Education and Science of the Russian Federation
125020401307-9

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