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Comparison of Bimacrocyclic, Monomacrocyclic, and Nonmacrocyclic Bis(amidomethyl)pyridines as Catalysts in the Base‐Catalyzed Addition of Alcohols to Ketenes
Author(s) -
Petersen Sönke,
Lüning Ulrich
Publication year - 1999
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/(sici)1099-0690(199904)1999:4<847::aid-ejoc847>3.0.co;2-3
Subject(s) - chemistry , catalysis , amide , propane , acylation , diol , organic chemistry , butane , base (topology) , alcohol , medicinal chemistry , mathematical analysis , mathematics
Nineteen new bimacrocyclic, monomacrocyclic, and nonmacrocyclic pyridines 1 – 6 bearing amide functions have been synthesized and utilized in base‐catalyzed additions of alcohols (ethanol, 2‐propanol) and polyols [propane‐1,2‐diol ( 11a ), butane‐1,3‐diol ( 12a ), methyl 4,6‐ O ‐benzylidene‐α‐ D ‐glucopyranoside ( 13a )] to diphenylketene. Compounds 4c , 4d and 1b proved to be efficient and selective catalysts; 4c and 4d exhibited better results with 11a and 12a , and 1b was the best catalyst for selective 2‐ O ‐acylation of 13a .