Synthesis of polyfused thieno(2,3-b)thiophenes part 2: Synthesis of thienopyrimidine, thienothiazine, thienopyrrolopiprazine, and thienothiazaphospholine derivatives

Article abstract of DOI:10.1080/10426500008076530

3,4-Diamino-2,5-dicarbethoxythieno(2,3-b)thiophene (1) was reacted with triethylorthoformate to afford compound 2. The reaction of compounds 2 or 3 with S,S-acetals and N,S-acetals, afforded compounds 4-6. Treatment of compound 1 with 2,5-dimethoxytetrahydrofuran gave the corresponding bipyrrolyl derivative 7, which was reacted with hydrazine hydrate to get the corresponding hydrazide derivative 8. Treating compound 8 with sodium nitrite afforded the corresponding carboazide derivative 9, which in turn cyclized to compound 10. Compound 12 was obtained via the reaction of compound 1 with PhNCS or through treating compound 11 with CS₂ PhNH₂, and KOH. Also, compound 13 was prepared through treatment of compound 12 with Lawesson's reagent or via the reaction of compound 11 with CS₂ followed by treating the resulting compound 14 with PhNH₂. The reaction of compounds 1 or 3 with Lawesson's reagent gave compound 15. Benzoylation of compound 1 afforded compound 16, which treated with NH₃ gave compound 17. Treatment of compounds 16 or 17 with LR furnished compounds 18 or 19, respectively. The reaction of compound 16 or 17 with P₂S₅ yielded compounds 19 and 20 or 18 and 19, respectively.

Full text of DOI:10.1080/10426500008076530

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Phosphorus, Sulfur, and
Silicon and the Related
Elements
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SYNTHESIS OF POLYFUSED
THIEN0(2,3-b)THIOPHENES
PART 2: SYNTHESIS OF
THIENOPYRIMIDINE,
THIENOTHIAZINE,
THIENOPYRROLOPIPRAZINE,
AND
THIENOTHIAZAPHOSPHOLINE
DERIVATIVES
H. Abdel-ghany a & A. Khodairy a
a Chemistry Department, Faculty of Science,
Sohag, Egypt
Available online: 19 Dec 2006
To cite this article: H. Abdel-ghany & A. Khodairy (2000): SYNTHESIS OF
POLYFUSED THIEN0(2,3-b)THIOPHENES PART 2: SYNTHESIS OF THIENOPYRIMIDINE,
THIENOTHIAZINE, THIENOPYRROLOPIPRAZINE, AND THIENOTHIAZAPHOSPHOLINE
DERIVATIVES, Phosphorus, Sulfur, and Silicon and the Related Elements, 166:1,
45-56
To link to this article: http://dx.doi.org/10.1080/10426500008076530
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