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The Aza Diels‐Alder Reaction on Brominated Conjugated Dienes
Author(s) -
Uceda Rafael G.,
RoldanMolina Esther,
Navarro Jorge A. R.,
Oltra J. Enrique
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100170
Subject(s) - chemistry , steric effects , conjugated system , diels–alder reaction , ring (chemistry) , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , polymer
The use of electron‐deficient dienes as substrates in the aza Diels‐Alder reaction (ADA) has been studied scarcely. However, the ADA process offers a wide range of applications in organic synthesis. In this communication, the reaction between different brominated conjugated dienes and 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione (PTAD), one of the most vigorous dienophiles, is reported. We have synthesized tricyclic compounds from acyclic substrates in only two steps, considering variables such as ring size and steric hindrance and substantially improved the results obtained with other dienophiles.