SUBSTITUTED "2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE AND 2,3,4,5-TETRAHYDRO-1H-NAPHTH[1,2-D]AZEPINE DERIVATIVES

The multi‐step synthetic procedures to prepare a number of 2,3,4,5‐tetrahydro‐1H‐benzazepine derivatives 1 through a series of intermediates are described. The condensation of arylaldehydes 2 with 2‐nitropropanes 3 gave nitroalcohols 4 which were reduced to alcohol amines 5. The condensation of 5 with arylacetaldehydes 6 gave imino derivatives 7 which on reduction with borohydride gave secondary amines 8. By employing different methods, alcohol amines 5 were condensed with arylacetic acids 9 to give amides 10 which were then reduced to amines 8. On treatment with mineral acids, amines 8 were cyclized to the target compounds 1. Biological activities of 1 are also briefly discussed. Copyright © 1979 Journal of Heterocyclic Chemistry