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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Construction of a 2,6-difunctionalized 2-methyl-2H-1-benzopyran library by using a solid-phase synthesis protocol
Jong Yeon Hwang1, Hyung-Sub Choi, Jin-soo Seo
1Medicinal Science Division, Korea Research Institute of Chemical Technology, P.O. Box 107, Yusung-gu, Daejeon 305-600, Korea.
Abstract:
[reaction: see text] A library containing 1200 analogues of 2,6-difunctionalized 2-methyl-2H-1-benzopyran was constructed by using a solid-phase synthesis protocol. Polymer-bound 6-amido-, 6-sulfonamido-, and 6-uredo-functionalized 2-hydroxymethyl-2-methylbenzopyrans 10 were prepared as part of a first-generation diversification step by employing reactions of respective acid halides, sulfonyl chlorides, and isocyanates with the amine precursor 7. Transformations of the resin-bound intermediates 10 by reactions with alkyl and acid halides were then used to produce a diverse series of 2,6-difunctionalized 2-methyl-2H-1-benzopyran analogues 12 and 14.
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