Base catalysed intermolecular cyclisation of N-protected o-amino benzaldehyde/acetophenone with phosphorus/sulphur based allenes: facile synthesis of substituted quinolines

被引:15
作者
Anitha, Mandala [1 ]
Gangadhararao, G. [1 ]
Swamy, K. C. Kumara [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
STEREOSELECTIVE-SYNTHESIS; ALLENYLPHOSPHINE OXIDES; PHOSPHINE OXIDES; BIOLOGICAL EVALUATION; CYCLOADDITIONS; HETEROCYCLES; BENZOFURANS; ANNULATIONS; DERIVATIVES; REACTIVITY;
D O I
10.1039/c6ob00259e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of N-Bz protected o-aminobenzaldehyde or acetophenone with allenylphosphonates in the presence of a simple base leads to quaternary carbon substituted phosphono-quinolines which undergo thermal rearrangement to O-phosphorylated quinolines. The present one-pot reaction involves intermolecular cyclisation, dehydration, and benzoyl group rearrangement followed by a novel phosphoryl group migration. The migration was less facile/not observed in the reactions using allenylphosphine oxides and sulphur based allenes wherein only substituted quinolines were obtained in good yields. X-ray structures have been determined for the key products.
引用
收藏
页码:3591 / 3602
页数:12
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