Synthesis and fluorescent properties of some Furan‐tagged Thienopyrimidines and Thienodipyrimidines

• Published in: Journal of heterocyclic chemistry Vol. 57; no. 5; pp. 2194 - 2202
• Main Authors: Abdel Hamid, Atef M, Hamed, Eman O
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc 01-05-2020
• Subjects: Acetylacetone; Carbon disulfide; Derivatives; Fluorescence; Formic acid; Pyrimidines; Reagents; Room temperature
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.3939

Intermolecular cyclization of pyrimidinethiol 1 with ethyl chloroacetate and chloroacetonitrile furnished thieno[2,3‐d]pyrimidines 2a,b. Hydrazinolysis of o‐aminoester 2a gave acid hydrazide 3, which was cyclized with various electrophilic reagents including formic acid, triethyl orthoformate, acetic anhydride, p‐chlorobenzaldehyde then triethyl orthoformate, carbon disulfide, and acetylacetone affording thienopyrimidine derivatives 4 to 10. Another thienopyrimidine series could be obtained via treatment of o‐aminocarbonitrile 2b with a variety of reagents giving derivatives 11 to 17. The fluorescent measurements for a group of the synthesized compounds at room temperature demonstrated high fluorescent properties.