ChemInform Abstract: 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.

Abstract

Fused pyrimidine derivatives R 0515Azirino[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. -Quantum-chemical calculations using the DFT B3LYP/ 6-31G(d) method confirm that the mechanism of the presented reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation. Mechanism and calculations are discussed in detail. The structure of product (IIIa) is proved by X-ray analysis. -(KADINA, A. P.; NOVIKOV, M. S.; KHLEBNIKOV*, A. F.; MAGULL, J.; Chem. Heterocycl. Compd. (N. Y.) 44 (2008) 5, 576-584; Fac. Chem., St. Petersburg State Univ., St. Petersburg 198504, Russia; Eng.) -H. Haber 23-158