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Hydrazones as Productive Dienophiles in the Inverse Electron Demand Diels–Alder Reactions of 1,3,5‐Triazines
Author(s) -
Yang Kai,
Yang Zhen,
Dang Qun,
Bai Xu
Publication year - 2015
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.201500499
Subject(s) - chemistry , triazine , substituent , reactivity (psychology) , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
Enamines, ynamines and amidines are common dienophiles for inverse electron demand Diels–Alder (IEDDA) reactions of 1,3,5‐triazines, however, their wide utilization may be limited due to their poor stability to conventional purification methods such as silica gel chromatography. To address this limitation, oximes and hydrazones are envisioned as potential alternative dienophiles, even though they are primarily used as protecting groups due to their excellent stability or lack of reactivity. Through investigation of substituent effects and optimization of reaction conditions, oximes and hydrazones were developed as productive dienophiles for 1,3,5‐triazine IEDDA reactions, leading to the desired IEDDA products in moderate (for oximes) to excellent (for hydrazones) yields. Hydrazones are air‐stable and can be conveniently purified by conventional methods, therefore the introduction of hydrazones as productive dienophiles further expanded the scope of 1,3,5‐triazine IEDDA reactions.