New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities

Alkyl pyrazole-1-carboxylates ( 2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated...

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Bibliographic Details
Published in:Tetrahedron 1998-12, Vol.54 (49), p.14679-14688
Main Authors: Kashima, Choji, Tsuruoka, Shiro, Mizuhara, Saori
Format: Article
Language:English
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Summary:Alkyl pyrazole-1-carboxylates ( 2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate ( 2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization. Alkyl pyrazole-1-carboxylates ( 2) were acted as the facile alkoxycarbonylating agent for preparation of one carbon higher carboxylic esters and the protection of amino acid derivatives.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00947-8