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C−C versus C−N Annulation Reactions of 2‐Alkyl‐2‐oxazolines and 2‐Alkyl‐2‐thiazolines: A Simple Synthesis of Novel 3‐Aminoindene, Phthalimidine, Pyrrolidine, and Piperidine Derivatives
Author(s) -
Fustero Santos,
Díaz Maria Dolores,
Carrió Juan Server,
Aguilar Enrique
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200103)2001:6<1195::aid-ejoc1195>3.0.co;2-2
Subject(s) - chemistry , alkyl , annulation , pyrrolidine , piperidine , organic chemistry , medicinal chemistry , catalysis
The effect of various aromatic and aliphatic dielectrophiles on the lithium azaenolates of 2‐alkyl‐2‐oxazolines and 2‐alkyl‐2‐thiazolines has been examined. This effect varies greatly, depending on the nature of the dielectrophile used. 3‐Aminoindene ( 3 ) and 3‐alkylidenephthalimidine ( 4−5 ) derivatives were formed as a result of the reactions with dielectrophiles derived from ortho ‐substituted benzonitriles. Similarly, 2‐alkylidenepyrrolidine ( 7 ) and 2‐alkylidenepiperidine ( 8 ) derivatives were obtained in high yields from 2‐alkyl‐2‐oxazolines or 2‐alkyl‐2‐thiazolines and aliphatic dielectrophiles derived from ω‐haloalkyldiphenylacetonitrile. C−C versus C−N annulation reactions are discussed.