Aziridine fused

Other types of ring-fused aziridines, fused at the 1,2-bond, similarly generate azomethine ylides whose skeleton is partially incorporated in a ring system (68JOC1097 69JOC171 86JCS(P1)1119). 

M. J. Robins, S. D. Hawrelak, T. Kanai, J. M. Siefert, and R. Mengel, Nucleic-acid related compounds. 30. Transformations of adenosine to the 1st 2, 3 -aziridine-fused nucleosides, 9-(2,3-epimino-2,3-dideoxy-P-D-ribofuranosyl)adenine and 9-(2,3- epimino-2,3-dideoxy-p-D-lyxo-furanosyl)adenine, J. Org. Chem., 44 (1979) 1317-1322. 

Using Vinyl Sulfonium Salts Aggarwal and coworkers have reported that the reaction of the a-, p-, or Y-aminoaldehydes 68 with diphenyl vinyl sulfonium salt 69 in the presence of a base gave the fused bicyclic heterocycles 70 (Scheme 4.15) [24]. This methodology has been extended to the asymmetric synthesis of seven-membered hexahydroazepine. Condensation of the hemiaminal 71 with (/ )-tert-butyl-sulfinamide [25] afforded the aminal 72, which was in equilibrium with sulfinylimine 73. Reaction of 72 with diphenyl vinyl sulfonium salt 69 in DMF using NaH as a base furnished the aziridine-fused hexahydroazepine 74 in 68% yield as a 3 1 mixture of diastereomers. Subsequent A-deprotection afforded the known chiral aziridine 75, an intermediate in the synthesis of (-)-balanol (76). 

Unthank, M. G., Hussain, N., Aggarwal, V. K. (2006). The use of vinyl sulfonium salts in the stereocontrolled asymmetric synthesis of epoxide- and aziridine-fused heterocycles application to the synthesis of (—)-balanol. Angewandte Chemie International Edition, 45, 7066-7069. 

SCHEME 6.7 Formation of aziridines-fused furobenzoxazocine or benzodiazocine. 

On heating the fused aziridine (461) at temperatures greater than 250 °C, the resultant product was the furo[3,4-[Pg.155]

The rearrangement of fused triazole (493) produced a fused aziridine and a fused 4-isoxazoline (494) (75T831). 

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