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Efficient Synthesis of Benzothieno[3,2-d]-1,2,4-triazolo [1,5-a]pyrimidin-5(1H)-ones via a Tandem aza-Wittig/Heterocumulene-Mediated Annulation

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成果类型:
期刊论文
作者:
Xu, Sheng-Zhen;Cao, Min-Hui;Chen, Chang-Shui;Ding, Ming-Wu*
通讯作者:
Ding, Ming-Wu
作者机构:
[Xu, Sheng-Zhen; Ding, Ming-Wu] Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
[Chen, Chang-Shui; Xu, Sheng-Zhen; Cao, Min-Hui] HuaZhong Agr Univ, Coll Basic Sci, Wuhan 430070, Peoples R China.
通讯机构:
[Ding, Ming-Wu] C
Cent China Normal Univ, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
语种:
英文
期刊:
Journal of Heterocyclic Chemistry
ISSN:
0022-152X
年:
2009
卷:
46
期:
5
页码:
903-908
基金类别:
National Natural Science Foundation of China [20772041]; Key Project of Chinese Ministry of Education [107082]; Doctors' Research Foundation of Huazhong Agricultural University [52204-07092]
机构署名:
本校为第一且通讯机构
院系归属:
化学学院
摘要:
(Chemical Equation Presented) The carbodiimides 2, obtained from reactions of iminophosphorane 1 with isocyanates, reacted with hydrazine to give selectively 3-amino-2-arylaminobenzothieno[3,2-d]pyrimidin-4(3H)-ones 4. Reactions of 4 with triphenylphosphine, hexachloroethane, and Et3N produced iminophosphoranes 5. A tandem aza-Wittig reaction of iminophosphorane 5 with isocyanate, acyl chloride generated benzothieno[3,2-d]-1,2,4-triazolo[1,5- a]pyrimidin-5(1H)-ones 7 and 9 in satisfactory yields. The effects of the nucleophiles on cy...

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