Transformation of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile into 4-aminopyrido[2,3-d]pyrimidines and 2-(pyrid-2-yl)guanidines

Add time:08/06/2019    Source:sciencedirect.com

The reactions of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile (14) with a range of primary and secondary amines are investigated. Treatment with n-BuNH2 and BnNH2 gave 1,3-di-n-butyl- and 1,3-dibenzyl-2-(3,5-dicyano-6-ethoxy-4-phenylpyrid-2-yl)guanidines 15a (32%) and 15b (82%), respectively. While treatment with Et2NH, n-Pr2NH or Bn2NH gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16c–e in high yields. Treatment of the dithiazole 14 with pyrrolidine, piperidine or morpholine gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16f–h, the 2-aminopyridine 13 and 2-(diamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitriles 15f–h. The 4-dialkylaminopyrido[2,3-d]pyrimidines 16f–h are converted to the 2-(dialkylamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitriles 15f–h upon further reaction with excess dialkylamines. The structure and origins of the two side products 17 and 18 are also discussed. Tentative mechanisms for these transformations are proposed.

We also recommend Trading Suppliers and Manufacturers of m-Chloro-1-cyanoformanilide (cas 15313-46-9). Pls Click Website Link as below: cas 15313-46-9 suppliers

Prev:Synthesis, characterization, stereochemistry and biological investigation of certain N-dichloroacetyl-bis(2-chlorophenyl)piperidin-4-ones
Next:The absorption, translocation, and metabolism of difenopenten-ethyl in soybean and wheat)