AZIRINO[c]IMIDAZOLYL YLIDES IN THE DOMINO REACTION OF 2,2-DIALKYL-4,6-DIARYL-1,3-DIAZABICYCLO[3.1.0]HEX-3-ENES WITH DICHLOROCARBENES. SYNTHESIS OF (1RS,5SR,6RS)-4-(ALK-1-ENYL)-1,5-DIARYL-3,7,7-TRICHLORO-2,4-DIAZABICYCLO[4.1.0]HEPT-2-ENES

被引：8

作者：

Kadina, A. P. ^{[1
]}

Novikov, M. S. ^{[1
]}

Khlebnikov, A. F. ^{[1
]}

Magull, J. ^{[2
]}

机构：

[1] St Petersburg State Univ, Fac Chem, St Petersburg 198504, Russia

[2] Univ Gottingen, Inst Inorgan Chem, D-37077 Gottingen, Germany

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2008年 / 44卷 / 05期

关键词：

aziridines; carbenes; imidazoles; iminium ylides; pyrimidines; cascade reactions; domino reactions;

D O I：

10.1007/s10593-008-0077-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbene to give (1RS,5SR,6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes has been studied. Quantum-chemical calculations using the DFT B3LYP/6-31G(d) method have confirmed that the mechanism of the reaction includes the formation of azirino[c] imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation.

引用

页码：576 / 584

页数：9