Journal of the Chemical Society. Chemical communications p. 1105 - 1107 (1984)
Update date:2022-08-17
Topics:
Boyd, Gerhard V.
Lindley, Peter F.
Nicolaou, George A.
The title salts, which are formed by the action of dimethylcyanamide on the phosphorus oxychloride complexes of a variety of tertiary amides, are useful precursors of six-membered heteroaromatic compounds: they react with simple amidines to yield 1,3,5-triazines and with N,N-dimethylamidines to give pyrimidines; 3-arylmethyl-1-chloro-1,3-bis(dimethylamino)-2-azapropenylium perchlorates form isoquinolines, the related 3-arylamino-1-chloro-1-dimethylamino-2-azapropenylium salts cyclise to quinazolinium salts, and treatment of 1-chloro-1,3-bis(dimethylamino)-3-phenyl-2-azapropenylium perchlorate with potassium thiocyanate results in a rearranged 1,3,5-thiadiazinium salt.
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