Efficient solid-phase synthesis of 2,4-disubstituted 5-carbamoyl-thiazole derivatives using a traceless support
- Authors
- Kim, Daehun; Baek, Dong Jae; Lee, Doohyun; Liu, Kwang-Hyeon; Bae, Jong-Sup; Gong, Young-Dae; Min, Kyung Hoon; Lee, Taeho
- Issue Date
- May-2015
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- 5-Carbamoyl-thiazole; Solid-phase synthesis; Combinatorial chemistry; Traceless support; Heterocycles
- Citation
- TETRAHEDRON, v.71, no.21, pp 3367 - 3377
- Pages
- 11
- Journal Title
- TETRAHEDRON
- Volume
- 71
- Number
- 21
- Start Page
- 3367
- End Page
- 3377
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/9550
- DOI
- 10.1016/j.tet.2015.03.104
- ISSN
- 0040-4020
- Abstract
- An efficient protocol for the solid-phase synthesis of 2,4-disubstituted 5-carbamoyl-thiazole derivatives has been developed. After the reaction scopes were investigated in solution-phase, the polymer-supported synthesis route was progressed using a sulfide linker in a traceless manner. The solid-phase synthetic protocol started with the Thorpe-Ziegler type cyclization of 2-chloroacetamide and polymer-bound cyanocarboimidodithioate, which is derived from Merrifield resin. The resulting 5-carbamoyl-thiazole was introduced to one substitution by N-acylation. After the oxidation of sulfides to sulfones for subsequent cleavage, nucleophilic desulfonative substitution with amines and thiols gave the target 2,4-disubstituted 5-carbamoyl-thiazole derivatives in good purities and overall yields. (C) 2015 Elsevier Ltd. All rights reserved.
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Collections - College of Pharmacy > School of Pharmacy > 1. Journal Articles
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