Synthesis of polyfused thieno(2,3-b)thiophenes part 1: Synthesis of thienopyrimidine derivatives

Article abstract of DOI:10.1080/10426500008045225

3,4-Diamino-2,5-dicarbethoxythieno(2,3-b)thiophene 1 reacted with malononitrile or ethyl cyanoacetate to afford bis(thienopyrimidin-4-one) derivatives 2a,b The reaction of compound 1 with o-aminothiophenol, o-aminophenol or o-phenylenediamine gave benzothiazolyl-, benzoxazolyl-, benzoimidazolylthienothiophene 3_a-c, Chloroacetylation of compound 1 and reacting the resulting compound 4 with malononitrile furnished thienopyrolopyrimidine 6. Fusion of compound 1 with formamide yielded bis(thienopyrimidine) 7 which reacted with POCl₃/PCl₅ to yield the corresponding chloro derivative 8 which was converted into the corresponding hydrazine derivative 9. Treatment of compound 1 with CS₂, NaOH and 1,2 dibromoethane produced the corresponding 1,3 dithiolane 11 which also treated with chloroacetyl chloride or ethyl mercaptoacetate to get the corresponding β-lactame 12 or thiazolidinone 13. On reacting compound I with CS₂, NaOH and (CH₃)₂SO₄ produced the corresponding bi(dithiocarbamate methyl ester) 14 which treated with hydrazine hydrate to yield the corresponding bis(thienopyrimidine) derivative 15. This compound reacted with Lawesson's reagent (LR) to give the desired compounds 16 and 17. While its reaction with (CH₃)₂ SO₄ and NaOH furnished the corresponding methyl derivative 18. Fusion of compound 18 with aniline afforded compound 19. Compound 19 was allowed to react with ethyl acetoacetate, acetylacetone, α-oxoketene dithioacetal, ethoxymethylene malononitrile or LR to get the described compounds 20_a-b-24 respectively.

Full text of DOI:10.1080/10426500008045225

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Phosphorus, Sulfur, and Silicon
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SYNTHESIS OF POLYFUSED
THIENO(2,3-b)THIOPHENES
PART 1: SYNTHESIS OF
THIENOPYRIMIDINE DERIVATIVES
A. Khodairy a & H. Abdel-ghany a
a Chemistry Department, Faculty of Science, Sohag,
Egypt
Available online: 04 Oct 2006
To cite this article: A. Khodairy & H. Abdel-ghany (2000): SYNTHESIS OF POLYFUSED
THIENO(2,3-b)THIOPHENES PART 1: SYNTHESIS OF THIENOPYRIMIDINE DERIVATIVES,
Phosphorus, Sulfur, and Silicon and the Related Elements, 162:1, 259-273
To link to this article: http://dx.doi.org/10.1080/10426500008045225
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