Nitriles in Heterocyclic Synthesis: Synthesis of Pyrido[3’,2’:4,5]Thieno[2,3-d] Pyrimidines Derivative - Open Access Library Journal

OALibJ > Vol.2 No.1, January 2015

Open Access Library Journal

Volume 2, Issue 1 (January 2015)

ISSN Print: 2333-9705 ISSN Online: 2333-9721

Google-based Impact Factor: 0.73 Citations

Nitriles in Heterocyclic Synthesis: Synthesis of Pyrido[3’,2’:4,5]Thieno[2,3-d] Pyrimidines Derivative ()

HTML XML

Download as PDF (Size: 2610KB) PP. 1-9

DOI: 10.4236/oalib.1101307 1,065 Downloads 1,739 Views Citations

Author(s)

Abdel Haleem Mostafa Hussein, Essam Abdel Raheem Eshak, Fathi Aly Abu-Shanab

Affiliation(s)

Chemistry Department, Faculty of Science, Al Azhar University, Assiut, Egypt.

ABSTRACT

6-Amino-3,5-dicyano-4-methylpyridine-2(1H)-thione 1 reacted with a-haloketones to give the Salkylated derivatives 2a-m. Compound 2a-m undergoes cyclization into thieno[2,3-d] pyridine derivatives 3a-m upon treatment with ethanolic sodium ethoxide. Saponification of 3a gave the amino acid 4 which afforded 5 when refluxed in Ac₂O. Treatment of 5 with NH₄OAc/AcOH gave 6a. Compound 6a also was obtained when 3c was refluxed in Ac₂O. Reaction of 3a with formamide gave 7 and with hydrazine hydrate gave 8. The thiourea derivative 9 was obtained by reaction of 3a with benzoyl isothiocyanate. Compound 9 when refluxed in alcoholic KOH gave 10 and with 98% H₂SO₄ gave 12. Acetylation of 3a with Ac₂O gave the acetyl derivative 13 which on treatment with aniline afforded 14. Compound 14 was cyclized with H₂SO₄ to 15. Finally treatment of compound 5 with aniline in AcOH afforded 6b.

KEYWORDS

Nitriles, Heterocyclic Synthesis

Share and Cite:

Hussein, A. , Eshak, E. and Abu-Shanab, F. (2015) Nitriles in Heterocyclic Synthesis: Synthesis of Pyrido[3’,2’:4,5]Thieno[2,3-d] Pyrimidines Derivative. Open Access Library Journal, 2, 1-9. doi: 10.4236/oalib.1101307.

Cited by

[1]	Синтез новых биологически активных конденсированных пиридинов на основе алициклических и гетероциклических кетонов
	2017

[2]	An efficient synthesis and antimicrobial and antifungal activities of disubstituted 3, 4-dihydro-2H-1, 3-thiazin-4-ones using lemon juice: A natural approach
	2017

[3]	ДАШЯН ШУШАНИК ШАМИРОВНА

Journals Menu

Follow SCIRP

	+1 323-425-8868
	customer@scirp.org
	+86 18163351462(WhatsApp)
	1655362766

	Paper Publishing WeChat

Journals Menu

Home

About SCIRP

Service

Policies