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Novel synthesis of pyrido[2,1‐ f ]‐ as ‐triazinium system and its zwitterionic derivatives. Different reactivities of 1‐ and 3‐olates with electrophiles
Author(s) -
Bátori S.,
JuhászRiedl Z. S.,
Sándor P.,
Messmer A.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230213
Subject(s) - chemistry , electrophile , formamide , boron trifluoride , medicinal chemistry , nucleophile , organic chemistry , boron , phosphorus , catalysis
A novel convenient synthesis of the title system has been developed using α‐carbonyl derivatives of N ‐aminopyridine and formamide (and its substituted derivatives) in the presence of phosphorus oxychloride or boron trifluoride. Quaternization of zwitterionic 1‐ and 3‐olates ( 4a, 4b; 11 ) with soft and hard methylating agents has been studied. Mechanistic suggestion are given to explain the formation of the different (solely N‐Me; N‐Me and O‐Me; solely OMe) products.