Stereoselective synthesis of (E)-halomethylidene[1,3]thiazolo[3,2-a]thieno[3,2-e]pyrimidinium and analogous [1,3]oxazolo[3,2-a]thieno[3,2-e]pyrimidinium halides starting from 3-N-substituted 2-propargylthio(oxy)thieno[2,3-d]pyrimidin-4-ones

Heterocyclic communications

article

Marina Slivka¹  Andrej Krivovjaz¹  Mikhailo Slivka¹  Vasil Lendel¹ 

[1] Laboratory of Organic Chemistry, Uzhgorod National University

关键词: electrophilic halocyclization;    [1;    3]oxazolo[3;    2-a]thieno[3;    2-e]pyrimidinium halides;    [1;    3]thiazolo[3;    2-a]thieno[3;    2-e]pyrimidinium halides;    stereoselective synthesis;   

DOI  :  10.1515/hc-2013-0036

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

A convenient procedure for the stereoselective synthesis of [1,3]thiazolo[3,2- a ]thieno[3,2- e ]pyrimidinium halides and analogous [1,3]oxazolo[3,2- a ]thieno[3,2- e ]pyrimidinium halides 5 and 6 is reported. 2-Propargylthio-3- R -thieno[2,3- d ]pyrimidin-4-ones and 2-propargyloxy-3- R -thieno[2,3- d ]pyrimidin-4-ones were treated with bromine or iodine in AcOH to afford ( E )-halomethylidene[1,3]thiazolo[3,2- a ]thieno[3,2- e ]pyrimidinium and ( E )-halomethylidene-[1,3]oxazolo[3,2- a ]thieno[3,2- e ]pyrimidinium halides, respectively.

【 授权许可】

CC BY|CC BY-NC-ND