2-甲硫基-7(5)-取代-3-吡唑并[1,5-a]嘧啶甲酸乙酯的区域选择性合成与2D NMR研究  

Regioselective Synthesis and 2D NMR Research of Ethyl 2-Methylthio-7(5)-substituted Pyrazolo[1,5-a]pyrimidine-3-carboxylate

作　　者：李明[1,2] 郭维斯[1] 文丽荣[1] 钟惠民[1] 杨华铮[3] 

机构地区：[1]青岛科技大学化学与分子工程学院 [2]南开大学元素有机化学国家重点实验室,天津300071 [3]南开大学元素有机化学国家重点实验室

出　　处：《化学学报》2005年第9期855-860,i003,共7页Acta Chimica Sinica

基　　金：国家重点基础研究发展规划(No.G1998040800);山东省自然科学基金(No.2003B01);国家自然科学基金(No.20172031)

摘　　要：利用3-甲硫基-4-乙氧羰基-5-氨基-1H-吡唑分别与甲基/芳基烯胺酮反应,合成了8种新的化合物2-甲硫基-7-取代-3-吡唑并[1,5-a]嘧啶甲酸乙酯(3a～3g)和2-甲硫基-5-甲基-3-吡唑并[1,5-a]嘧啶甲酸乙酯(4a).化合物的结构均经元素分析,IR,1HNMR,MS所证实,异构体3a和4a的结构进一步由13CNMR,HMQC和HMBC确认.同时,探讨了区域选择性合成吡唑并[1,5-a]嘧啶类化合物可能的反应机理,并对部分化合物杀菌活性进行了测试.By the reaction of 3-methylthio-4-ethoxycarbonyl-5-aniino-lH-pyrazole with substituted enaminones, eight new compounds of ethyl 2-methylthio-7-substituted pyrazolo[1,5-a]pyrimidine-3-carboxylate (3a similar to 3g) and elhyl 2-methylthio-5-methyl pyrazolo[1,5-a]pyrimidine-3-carboxylate (4a) have been synthesized respectively. The structures of all compounds were characterized by elemental analyses, IR, H-1 NMR, and MS. Structures of regioisomer 3a and 4a were further determined by C-13 NMR, HMQC and HMBC. In the meantime, the plausible mechanism for regioselective synthesis of pyrazolo[1,5-a]pyrimidine was discussed. The preliminary test showed that some of the compounds had somewhat antifungal activities.

关 键 词：区域选择性合成 甲酸乙酯 甲硫基 2DNMR 吡唑 化合物 乙氧羰基 元素分析 ^13C HMBC HMQC 反应机理 杀菌活性 ^1H 异构体 嘧啶类 甲基 结构 烯胺 芳基 IR 酮 

分 类 号：O621.25[理学—有机化学]