Efficient Synthesis of Pyrimido[1,2-c] [1,3]benzothiazin-6-imines and Related Tricyclic Heterocycles by SNAr-Type C-S, C-N, or C-O Bond Formation with Heterocumulenes
Efficient Synthesis of Pyrimido[1,2-c] [1,3]benzothiazin-6-imines and Related Tricyclic Heterocycles by SNAr-Type C-S, C-N, or C-O Bond Formation with Heterocumulenes
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DOI：
10.1021/jo902327n
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发表时间：
2010-01-01
影响因子：
3.6
通讯作者：
Ohno, Hiroaki
中科院分区：
文献类型：
--
作者：
Mizuhara, Tsukasa;Oishi, Shinya;Ohno, Hiroaki
本文报道了一种简单实用的嘧啶并[1，2-c]-[1，3]苯并噻嗪-6-亚胺及其三环杂环化合物的合成方法。在DMF中用NaH和杂枯烯如二硫化碳、异硫氰酸酯和异氰酸酯处理2-（2-卤代芳基）-四氢嘧啶通过区域选择性SNAr型反应提供所需的环化产物。该方法可直接获得PD 404182和相关化合物。
A simple and practical synthetic method of pyrimido[1,2-c]-[1,3]benzothiazin-6-imines and related tricyclic heterocycles has been developed. Treatment of 2-(2-haloaryl)-tetrahydropyrimidines with NaH and a heterocumulene such as carbon disulfide, isothiocyanates, and isocyanates in DMF provides the desired cyclization products through a regioselective SNAr-type reaction. This method provides direct access to PD 404182 and related compounds.