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The reactions of some pyraiiylideneiminium salts with amines. II
Author(s) -
Van Allan J. A.,
Chang S. Chie,
Reynolds G. A.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090610
Subject(s) - chemistry , iminium , amine gas treating , pyridinium , medicinal chemistry , perchlorate , pyridine , salt (chemistry) , primary (astronomy) , ammonia , benzopyran , ring (chemistry) , derivative (finance) , organic chemistry , ion , physics , astronomy , financial economics , economics
The iminium salt, N,N ‐dimethyl‐ N ‐[2‐(2‐phenyl‐4 H ‐l‐benzopyran‐4‐ylidene)ethylidene] imin‐ium perchlorate ( 3 ), reacts with secondary amines by exchanging the dimethylimino group for the added amine. Primary amines also reacted with 3 in the same manner. The bis iminium salts, N,N,N',N' ‐tetramethyl‐ N,N '‐[2‐(2‐phenyl‐4 H ‐l‐benzopyran‐4‐ylidene)‐1,3‐propanediylidene]‐bis(immium perclilorate) ( 4 ) and the corresponding thiapyran derivative ( 5 ), react with ammonia to give 5‐dimethylamino‐2‐phenyl‐5 H ‐1‐benzopyrano[3,4‐ c ]pyridine ( 10 ) and the thia analog 11 . The reactions of 4 and 5 with primary amines give 3‐alkyl‐5‐dimethylamino‐2‐phenyl‐5 H ‐l‐beiizopyrano[3,4‐ c ]pyridinium perclilorate salts or the corresponding thiapyrano compounds. Compounds 4 and 5 react with secondary amines by exchanging the dimethylimino groups with the secondary amine and addition of the amine at the 2‐position of the pyran or thiapyran ring.