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4,4‐Disubstituierte Imidazol‐Derivate aus der Umsetzung von 3‐Amino‐2 H ‐azirinen mit Salicylamid
Author(s) -
Magirius Florian,
Linden Anthony,
Heimgartner Heinz
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770206
Subject(s) - chemistry , salicylamide , azirine , medicinal chemistry , imidazole , toluene , stereochemistry , organic chemistry , ring (chemistry)
4,4‐Disubstituted Imidazole Derivatives from the Reaction of 3‐Amino‐2 H ‐azirines with Salicylamide Reaction of 3‐amino‐2 H ‐azirines 1a–c with salicylamide ( 7 ) in MeCN leads to imidazoles 10 and 11 in different rates, depending on the conditions. In the case of 1a and 1b, 11a and 11b , respectively, have been obtained as the main product at 50°; in reactions at 80°, 10a and 10b are the favored products ( Tables 1 and 2 ). 2,2‐Dimethyl‐3‐( N ‐methyl‐ N ‐phenylamino)‐2 H ‐azirine ( 1c ) reacts with 7 in MeCN mainly to 2‐(2‐hydroxyphenyl)‐5,5‐dimethyl‐3,5‐dihydroimidazol‐4‐one ( 10a ); in boiling toluene, 11c is formed with low preference ( Table 3 ). The structure of the products has been established by spectroscopic means, and in the case of 10b and 11c , by X‐ray crystallography. Two different reaction mechanisms for the formation of the products are discussed ( Scheme 2 ).