Journal
TETRAHEDRON
Volume 74, Issue 3, Pages 392-400Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.11.071
Keywords
Nitrogen heterocycles; Breslow intermediate; Alkanoylation; Natural bond orbital; C-C bond formation
Categories
Funding
- Japan Society for the Promotion of Science
- MEXT, Japan [24105529]
- Rikkyo SFR project
- MEXT Supported Program for the Strategic Research Foundation at Private Universities
- Grants-in-Aid for Scientific Research [24105529, 15K07868, 17KT0010] Funding Source: KAKEN
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A combined experimental and computational study on the key intermediates of NHC-catalyzed acylation reaction, Breslow intermediates (BIs), has been conducted in order to achieve a direct nucleophilic alkanoylation of N-heterocycles. Various BI precursors are alternatively prepared and used in the reaction with 4-chloroquinazoline. The present study reveals that the intermediates having benzimidazole moiety serve as acylating agents for the introduction of straight-chain alkanoyl groups. Natural bond orbital analysis indicates that the reactivity of intermediates partly correlates to the occupancy of the pi(C-C) bonds of the hydroxyl enamine moieties. The putative rate-determining step of the acylation reaction has been theoretically investigated. Several new 4-alkanoylquinazolines are synthesized using the BI precursors. (C) 2017 Elsevier Ltd. All rights reserved.
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