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Generation and reactivity of N,N ‐dimethylaminobenzotriazolylcarbene a new nucleophilic carbene
Author(s) -
Katritzky Alan R.,
Cheng Dai,
Leeming Peter,
Ghiviriga Ion,
Hartshorn Chris M.,
Steel Peter J.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330662
Subject(s) - chemistry , carbene , cycloaddition , nucleophile , reactivity (psychology) , isocyanate , furan , medicinal chemistry , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , polyurethane
N,N ‐Dimethylaminobenzotriazolylcarbene ( 5 ) reacted with phenyl isocyanate in a [1+2+2] cycloaddition and then with nucleophiles to generate various hydantoins 10 in a one‐pot procedure. It was also found that this novel carbene reacted with trans ‐dibenzoylethylene ( 11 ) in a [1+4] cycloaddition, generating 2‐dimethylamino‐3‐benzoyl‐5‐phenylfuran ( 13 ) and 2‐phenyl‐3‐[benzotriazol‐1‐yl]‐4‐benzoylfuran ( 14 ) whose structures were confirmed by 1 H‐ 13 C long range correlations as well as the structure of furan 14 being confirmed by X‐ray crystallography.