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1,3‐Dipolare Cycloaddition aromatischer Nitril‐ylide und Nitril‐oxide an Dicyan und Diazocyanide
Author(s) -
Ried Walter,
Fulde Maria
Publication year - 1988
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.19880710714
Subject(s) - chemistry , benzonitrile , nitrile , cycloaddition , medicinal chemistry , ylide , organic chemistry , catalysis
1,3 Dipolar Cycloaddition of Aromatic Nitrile Ylides and Nitrile Oxides with Cyanogen and Diazocyanides Nitril ylides 2 generated from the imidoyl chlorides 1 react with cyanogen and aryldiazocyanides to 2,5(4)‐dia‐ryl‐1 H ‐imidazole‐4(5)‐carbonitriles 3a , b or 5(4)‐(arylazo)‐2,4(5)‐diaryl‐1 H ‐imidazoles 4a and 2,3,5‐triaryl‐2,3‐dihydro‐1 H ‐1,2,4‐triazole‐1‐carbonitriles 5a – f , respectively ( Scheme 1 ). Reactions of benzonitrile oxides 7 with these dipolarophiles lead to 3,3′‐diaryl‐5,5′‐bi[1,2,4]oxadiazoles 8a – c or 3‐aryl‐5‐(arylazo)‐1,2,4‐oxadiazoles 9a – j ( Scheme 2 ).