1,3‐Dipolare Cycloaddition aromatischer Nitril‐ylide und Nitril‐oxide an Dicyan und Diazocyanide | Zendy

Ried Walter | Zendy; Fulde Maria | Zendy

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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 ).

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