SYNTHESIS AND REGIOSELECTIVE [4+2] CYCLOADDITION NUCLEOPHILIC REACTIONS OF N-ARYLAMINO-1,3-DIAZA-1,3-BUTADIENES WITH KETENES AND ACCOMPANYING REARRANGEMENTS

被引：27

作者：

DEY, PD ^{[1
]}

SHARMA, AK ^{[1
]}

RAI, SN ^{[1
]}

MAHAJAN, MP ^{[1
]}

机构：

[1] NE HILL UNIV,DEPT CHEM,SHILLONG 793003,MEGHALAYA,INDIA

来源：

TETRAHEDRON | 1995年 / 51卷 / 27期

关键词：

D O I：

10.1016/0040-4020(95)00372-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Arylamino-1,3-diaza-1,3-butadienes 4 are shown to undergo regioselective reactions with phenyl- and chlorokete resulting in high yields of 3-aryl-2-methylthio-6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinirum intermediates 12, in good yields of 3-aryl-5-(N-arylamino)-2-methylthio-6-phenyl-4(3H)-pyrimidinones 13. The mechanistic aspects of cycloadditions and semi-empirical AM1 calculations for these diazabutadienes are also reported.

引用

页码：7459 / 7468

页数：10

共 13 条

[1]

BARLUENGA J, 1989, SYNTHESIS-STUTTGART, P228

[2] 1,4-CYCLOADDITION OF 1,3-DIAZABUTADIENES WITH ENAMINES - AN EFFICIENT ROUTE TO THE PYRIMIDINE RING [J].