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Transamidation reactions. Part 11 . N ‐substituted 3‐aminopropanenitriles and 2‐aminoacetonitriles as Schiff ‐base equivalents
Author(s) -
Askitoǧlu Elefteria,
Guggisberg Armin,
Hesse Manfred
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680325
Subject(s) - chemistry , schiff base , imine , nucleophile , base (topology) , formaldehyde , acetonitrile , mannich base , medicinal chemistry , bicyclic molecule , aldimine , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
In presence of a strong base, the 13‐membered cyclic compound 3 yielded, by loss of acetonitrile or its equivalent, the bicyclic product 5 instead of the 17‐membered compound 4 as expected (Scheme 2) . Investigation of model compounds (Scheme 4) and of model reactions ( Schemes 5 and 6 ) led to the conclusion that the reaction proceeds via an intermediate formaldehyde imine; a Schiff base, e.g. 3b (Scheme 5) , which reacts intra‐ and intermolecularly with a nucleophile to form a Mannich ‐type product. It seems to be a general principle that N ‐substituted 3‐aminopropanenitrile and 2‐aminoacetonitrile derivatives behave in the presence of a strong base as Schiff ‐base equivalents ( Schemes 5 and 6 ).