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Reactions of Azides with Electrophiles: New Methods for the Generation of Cationic 2‐Azabutadienes. Synthesis of 1,2, 3,4‐Tetrahydroquinolines and 1,2‐Dihydroquinolines via a Hetero Diels–Alder Reaction
Author(s) -
Pearson William H.,
Fang WenKui
Publication year - 1997
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199700007
Subject(s) - chemistry , electrophile , cationic polymerization , diels–alder reaction , organic chemistry , combinatorial chemistry , catalysis
Two methods for the generation of iminium ions of the type ArN + (X)=CHR (X = H or alkyl, R = H or alkyl) are reported: (1) the Bronsted‐acid‐promoted rearrangement of benzylic azides and (2) the intermolecular Schmidt reactions of azides XN 3 (X = aliphatic) with benzylic carbocations derived from benzylic alcohols ArCH(R)OH. The iminium ions ArN + (X)=CHR behave as cationic 2‐azabutadienes in the presence of alkenes and alkynes, producing 1,2, 3,4‐tetrahydroquinolines and 1,2‐dihydroquinolines by a hetero Diels–Alder reaction.