Studies on the mannich reaction of substituted catechol I:

Abstract

Mannich reaction of 3-[N,N-bis(carboxymethyl)aminomethyl]catechol (I) with piperidine, pyrroline, diethylamine, morpholine and piperazine gave the corresponding 5-substituted Mannich bases. The orientation of this Mannich reaction was explained through the intramol. hydrogen bonding of the starting material. However, the reaction of I with iminodiacetic acid or 3-(morpholinomethyl)catechol with morpholine gave the normal 6-substituted Mannich bases.

Key words: PIPERIDINE P, REACTION MECHANISM, INFRARED SPECTROPHOTOMETRY, NMR SPECTROMETRY, FORMALDEHYDE, HYDROGEN BONDS, BENZENEDIOL P, ACETIC ACID P, MANNICH REACTION, MORPHOLINE

CLC Number:

O621

Cite this article

LIANG CHENGYI;XUE FEN. Studies on the mannich reaction of substituted catechol I:[J]. Acta Chimica Sinica, 1987, 45(1): 99-102.

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取代邻苯二酚Mannich反应研究I: