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DBU‐Catalyzed [3+3] and [3+2] Annulation Reactions of Azomethine Ylides with α‐Diazocarbonyls as N ‐Terminal Electrophiles: Modular, Atom‐Economical Access to 1,2,4‐Triazine and 1,2,4‐Triazole Derivatives
Author(s) -
Zhang Lu,
Chen JiaJia,
Liu ShaSha,
Liang YongXin,
Zhao YuLong
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800030
Subject(s) - chemistry , electrophile , annulation , nucleophile , catalysis , intramolecular force , triazine , intermolecular force , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , molecule
The DBU‐catalyzed [3+3] and [3+2] cyclization reactions of azomethine ylides with α‐diazocarbonyls as N ‐terminal electrophiles have been developed. These reactions involve a sequential intermolecular nucleophilic addition/intramolecular cyclization/oxidation procedure. By the assembly of readily available starting materials, these transformations offer novel, highly efficient one‐pot syntheses of various functionalized 1,2,4‐triazine and 1,2,4‐triazole derivatives in an atom‐economical manner under ambient and metal‐free conditions in a high regio‐ and diastereoselective manner.