Amidines. I. Hydrolysis of N1-acyl- and N1-tosyl-N1,N2-diarylamidines

Article abstract of DOI:10.1248/cpb.38.590

In acid hydrolysis of N¹-acyl-N¹,N²-diarylamidines, a water molecule attacked exclusively the amidine central carbon, and the reaction proceeded in parallel through two pathways. One of them leads to the formation of two N-acylarylamines, and the other leads to the formation of N,N-diacylarylamine and arylamine. Acid hydrolysis of N¹-tosyl-N¹,N²-diarylamidine was also examined. The results were similar to those of the hydrolysis of N¹-acyl-N¹,N²-diarylamidines. Alkaline hydrolysis and alcoholysis of N¹-acyl-N¹,N²-diarylamidines occurred almost exclusively at the amide carbonyl group to give N¹,N²-diarylamidines and carboxylic acids or their esters. The effects of structural change and the aryl substituents on the rate and direction of the reaction were examined.

Full text of DOI:10.1248/cpb.38.590

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