Application of bis(iminophosphorane) in heterocyclic synthesis:: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones

被引：131

作者：

Ding, MW ^{[1
]}

Xu, SZ ^{[1
]}

Zhao, JF ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 24期

关键词：

D O I：

10.1021/jo048691v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The bis(carbodiimides) 4, obtained from bis-aza-Wittig reactions of bis(iminophosphorane) 3 with 2 equiv of aromatic isocyanates, were reacted with secondary amine to give symmetrically substituted 2,7-diaminothieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-dione 6 in the presence of a catalytic amount of EtO-Na+ Reactions of 4 with phenols or ROH in the presence of a catalytic amount of potassium carbonate or RO-Na+ gave symmetrically substituted 2,7-diaryl(alkyl)oxythieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 6 in satisfactory yields. However, iminophosphoranes 9 were obtained via reaction of bis(iminophosphorane) 3 with 1 equiv of aromatic isocyanate and subsequent reaction with an amine in the presence of a catalytic amount of EtO-Na+. Further reaction of iminophosphoranes 9 with aromatic isocyanates and various nucleophile generated unsymmetrically substituted thieno[2,3-d:5,4-d']dipyrimidine-4,5(3H,6H)-diones 12 in good yields.

引用

页码：8366 / 8371

页数：6

共 35 条

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