GENERATION AND REACTIVITY OF N,N-DIMETHYLAMINOBENZOTRIAZOLYLCARBENE ANEW NUCLEOPHILIC CARBENE

Authors
KATRITZKY AR CHENG D LEEMING P GHIVIRIGA I HARTSHORN CM STEEL PJ
Citation
Ar. Katritzky et al., GENERATION AND REACTIVITY OF N,N-DIMETHYLAMINOBENZOTRIAZOLYLCARBENE ANEW NUCLEOPHILIC CARBENE, Journal of heterocyclic chemistry, 33(6), 1996, pp. 1935-1941
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
33
Issue
6
Year of publication
1996
Pages
1935 - 1941
Database
ISI
SICI code
0022-152X(1996)33:6<1935:GARONA>2.0.ZU;2-9
Abstract
N,N-Dimethylaminobenzotriazolylcarbene (5) reacted with phenyl isocyan ate 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 t his 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 structu res were confirmed by H-1-C-13 long range correlations as well as the structure of furan 14 being confirmed by X-ray crystallography.