In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 56, No. 11 ( 1991), p. 2340-2351
Abstract:
trough the use of Pd(0)-catalyzed coupling between 2- and 4-formyl-3-thiopheneboronic acids and 3-amino-2-bromopyridine and 4-acetamido-3-bromopyridine, convenient one-pot procedures for the preparation of thieno[2,3- c ]-1,5-naphthyridine, thieno[3,4- c ]-1,5-naphthyridine, thieno-[2,3- c ]-1,6-naphthyridine, and thieno[3,4- c ]-1,6-naphthyridine have been developed. In order to obtain thieno[3,2- c ]-1,6-naphthyridine 2-(tributylstannyl)-3-thiophene aldehyde had to be used, since the organometallic partner in the coupling reaction, 3-formyl-2-thipheneboronic acid, is too easily deboronated. The effect of silver(I) oxide and thallium(I) carbonate on the coupling was studied. 1 H and 13 C NMR spectra of the six isomeric thieno{ c ]-fused 1,5- and 1,6-naphthyridines are discussed.
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc19912340
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
1991
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