Aziridinyl ketones and their cyclic anils. 9. Substituted 1,3-diazabicyclo[3.1.0]hex-3-enes

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

“…Compounds 1a,b were prepared by the method reported in [34] and compound 1c by that in [33]. Quantum-chemical calculations were made using the Gaussian 03 program package [35].…”

“…The dichlorocarbene was generated by basic hydrolysis of chloroform under phase transfer catalytic conditions (CHCl 3 /KOH / BnEt 3 NCl). The diazabicyclohexenes 1a-c which show interest as photochromic compounds can be readily prepared from the corresponding chalcone dibromide and ketone R 2 C(O)CH 2 R 3 in the presence of ammonia [33,34].…”

“…Bond lengths (l) and Valence Angles (ω) in the 1,3-Diazabicyclo[3.1.0]hex-3-ene Systems of Molecule 1d (Calculated Data) and 1b (X-ray Analytical Data[34]). …”

Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination

“…Starting from the α,β‐chalcone dibromides 2 , formaldehyde (or acetone) and with excess of ammonia, aryl‐substituted 1,3‐diazabicyclo[3.1.0]hex‐3‐enes 12 & 13 were obtained in one step without isolation of aziridinyl ketones 11 as reaction intermediate (Scheme ) …”

“…[33] Starting from the α,β-chalcone dibromides 2, formaldehyde (or acetone) and with excess of ammonia, aryl-substituted 1,3diazabicyclo[3.1.0]hex-3-enes 12 & 13 were obtained in one step without isolation of aziridinyl ketones 11 as reaction intermediate (Scheme 7). [34] Orlov and co-workers synthesized another derivatives of 5,7-diaryl-1,4-diazabicyclo[4.1.0]hepta-4-ene derivatives 15 having photochromic property by reaction of 1-aryl-3-(4-nitrophenyl)-2,3-dibromopropan-l-ones 2 with ethylenediamine 14 in the presence of N,N-dimethylbenzylamine (Scheme 8). [35] Chebanov and co-workers disclosed another convenient and straightforward synthesis of photochromic 2-aryl-1-(4nitrophenyl)-1,1a-dihydroazireno[1,2-a]quinoxaline derivatives Mixture of regioisomers are obtained when reaction of various 1,3-diaryl-2,3-dibromopropan-1-ones 2 performed with 4-methyl 1,2-phenylenediamine (Table 3) but single product is obtained in case of 4,5-dimethyl 1,2-phenylenediamine.…”