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Synthesis of New Azocine Derivatives and Their Functionalization by Nucleophilic Addition to Their Iminium Salts
Author(s) -
Leal Badaró Trindade Angela Cristina,
dos Santos Daniela Cristina,
Gil Laurent,
Marazano Christian,
Pereira de Freitas Gil Rossimiriam
Publication year - 2005
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/ejoc.200400728
Subject(s) - iminium , chemistry , regioselectivity , nucleophile , azide , reagent , nucleophilic addition , alkyl , adduct , hydride , methanesulfonic acid , trimethylsilyl azide , tetrafluoroborate , organic chemistry , medicinal chemistry , combinatorial chemistry , ionic liquid , ion , metal , catalysis
A route to the eight‐membered nitrogen heterocycles 20a , b is described starting from the 3‐alkyl‐ N ‐benzylpyridinium salts 14a , b . These azocine derivatives were converted into their respective iminium salts 11 by treatment with methanesulfonic acid. A study concerning the regioselectivity of nucleophilic additions to these salts is presented. Nucleophiles like hydride or Grignard reagents react selectively in the 2‐position to give adducts such as 22 and 23 , while azide and phenylthiolate attack the 6‐position to give 24 and 25 , respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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