Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines

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Title:Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines
Creators:
Gronowitz, Salo
Malm, Johan
Hörnfeldt, Anna-Britta
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 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-<i>c</i>]-1,5-naphthyridine, thieno[3,4-<i>c</i>]-1,5-naphthyridine, thieno-[2,3-<i>c</i>]-1,6-naphthyridine, and thieno[3,4-<i>c</i>]-1,6-naphthyridine have been developed. In order to obtain thieno[3,2-<i>c</i>]-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. <sup>1</sup>H and <sup>13</sup>C NMR spectra of the six isomeric thieno{<i>c</i>]-fused 1,5- and 1,6-naphthyridines are discussed.

Title:Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines
Creators:
Gronowitz, Salo
Malm, Johan
Hörnfeldt, Anna-Britta
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2340-2351
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912340UNSPECIFIED
ID Code:5163
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Gronowitz, Salo; Malm, Johan; Hörnfeldt, Anna-Britta (1991) Synthesis of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2340-2351. ISSN 0010-0765

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