7.
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).
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