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Reactions of β‐Azolylenamines with Sulfonyl Azides as an Approach to N ‐Unsubstituted 1,2,3‐Triazoles and Ethene‐1,2‐diamines
Author(s) -
Efimov Ilya,
Bakulev Vasiliy,
Beliaev Nikolai,
Beryozkina Tetyana,
Knippschild Uwe,
Leban Johann,
ZhiJin Fan,
Eltsov Oleg,
Slepukhin Pavel,
Ezhikova Marina,
Dehaen Wim
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402130
Subject(s) - chemistry , sulfonyl , azide , acetonitrile , aryl , solvent , medicinal chemistry , tosyl , organic chemistry , alkyl
The reactions of β‐azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1 H ‐4‐(azol‐5‐yl)‐1,2,3‐triazoles 3 in yields of 52–93 %. β‐Benzoylenaminones and β‐nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3 , proving the generality and efficiency of the method for the synthesis of N ‐unsubstituted 1,2,3‐triazoles. On the other hand, the reactions of 3‐(1‐aryl‐1,2,3‐triazol‐5‐yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of ( E )‐1‐dimethylamino‐2‐tosylaminoethenes 5 and N , N ‐dimethyl‐ N′ ‐tosylformamidine 6 in yields of 40–50 and 20 %, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5‐dimethylamino‐1,2,3‐triazolines 7 .