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

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 ava...

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Veröffentlicht in:Advanced synthesis & catalysis 2018-06, Vol.360 (11), p.2172-2177
Hauptverfasser: Zhang, Lu, Chen, Jia‐Jia, Liu, Sha‐Sha, Liang, Yong‐Xin, Zhao, Yu‐Long
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container_issue 11
container_start_page 2172
container_title Advanced synthesis & catalysis
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creator Zhang, Lu
Chen, Jia‐Jia
Liu, Sha‐Sha
Liang, Yong‐Xin
Zhao, Yu‐Long
description 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.
doi_str_mv 10.1002/adsc.201800030
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subjects 1,2,4-triazines
1,2,4-triazoles
azomethine ylides
Chemical reactions
Derivatives
N-terminal electrophiles
Organic chemistry
Oxidation
α-diazocarbonyls
title 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
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