o‐Monobromoacetylacylphenones, 3a and 3b reacted with hydroxylamine or hydrazine hydrate to produce heterocycles, 2,3‐benzoxazine or phthalazine derivatives. The reaction of bromoacetyl group of 3a and 3b with several thioamides afforded thiazole derivatives in high yields. Whereas o‐dibromoacetyl‐benzophenoe 2a reacted with aniline or cyclohexylamine to produce non‐heterocycles, 2‐substituted‐iminophenylindanones and the mechanism for the formation of these non‐heterocycles is proposed.
2‐Bromo‐3‐phenylinden‐1‐one 2 reacted with phenylthiourea to produce 2‐phenylimino‐8‐phenylindeno[1,2‐d]thiazole (heteropentalene) 4 in moderate yield and bis‐substituted‐indenyl sulfide 5 in low yield. Whereas, from the reaction of 2 with thiourea or its methyl derivative only 5 was obtained in moderate yield. Another brominated compound, dibromoacetylbenzophenone and several primary amines afforded iminoindanone derivatives 6.
o‐Dibromoacetylbenzophenone, 2 or o‐bromoacetylbenzophenone 3 reacted with aqueous ammonia to produce 3‐phenylisoindolin‐1‐one 5. The reaction of 3 with methylamine afforded 3‐hydroxy‐2‐methyl‐3‐phenyl‐isoindolin‐1‐one 4 and 2‐methyl‐3‐phenylisoindolin‐1‐one 5. Whereas from 2 with methylamine only 5 was obtained.
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