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On the protonation and deuteration of N , N ‐disubstituted 2‐aminothiophenes, 2‐aminothiazoles, and some 3‐amino substituted analogues
Author(s) -
Heichert Christoph,
Hartmann Horst
Publication year - 2021
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.4279
Subject(s) - chemistry , protonation , aniline , thiophene , cationic polymerization , electrophile , electrophilic substitution , deuterium , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion , physics , quantum mechanics
In contrast to their carbocyclic aniline analogues, N , N ‐diarylsubtituted 2‐aminothiophenes are not protonated at their N ‐atoms but at the 5‐position or, to a smaller extent, at the 3‐position of the thiophene nucleus giving rise to cationic species of the Wheland type. However, 5‐formyl and 5‐acetyl‐substituted 2‐( N , N ‐diarylamino)thiophenes are protonated at the corresponding carbonyl moieties. This finding not only enables insight into the mechanism of electrophilic substitution of N , N ‐disubstituted 2‐aminothiophenes but also allows to prepare deurated 2‐aminothiophenes by treatment their non‐deuterated parent compounds with CF 3 COOD.