Efficient Synthesis of 6-(1H-1,2,4-Triazol-1-yl)-thieno[2,3-d]pyrimidin- 4(3H)-ones via an Iminophosphorane

Synthetic Communications

Volumn 40, Issue 13, 2010, Pages 1985-1991

  Sun, Yong ^a,b   Huang, Nian Yu ^a   Ding, Ming Wu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b YUNYANG TEACHERS COLLEGE   (China)

Author keywords

1,2,4 triazole; Aza Wittig reaction; Gewald reaction; Iminophosphorane; Thieno 2,3 d pyrimidin 4(3H) one

Indexed keywords

6 (1H 1,2,4 TRIAZOL 1 YL)THIENO[2,3 D]PYRIMIDIN 4(3H)ONES; CYANAMIDE; ISOCYANATE; PHOSPHORANE DERIVATIVE; PYRIMIDINE DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 77953457169     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903219351     Document Type: Article

References (14)

1. Walter, H. 4-Pyrimidinones and 4-pyrimidinethiones as agricultural fungicides. WO Patent 9911631, 1999. Chem. Abstr. 1999, 130, 237580e.
2. Aboulwafa, O. M.; Ismail, K. A.; Koreish, E. A. Synthesis and antimicrobial activity of some thiazolinyl tetrahydrobenzo[b]thiophenes and thiazolinyl tetrahydrobenzothie-no[2,3-d] pyrimidin-4-ones. Farmaco 1992, 47, 631-642.
3. Hozien, Z. A.; Atta, F. M.; Hassan, Kh. M.; Abdel-Wahab, A. A.; Ahmed, S. A. Synthesis and application of some new thienopyrimidine derivatives as antimicrobial agents. Synth. Commun. 1996, 26, 3733-3755.
4. Chambhare, R. V.; Khadse, B. G.; Bobde, A. S.; Bahekar, R. H. Synthesis and preliminary evaluation of some N-[5-(2-furanyl)-2-methyl-4-oxo-4H-thieno[2, 3-d]pyrimidin-3-yl] carboxamides and 3-substituted 5-(2-furanyl)-2-methyl-3H- thieno[2,3-d]pyrimidin-4-ones as antimicrobial agents. Eur. J. Med. Chem. 2003, 38, 89-100.
5. Kikuchi, H.; Yamamoto, K.; Horoiwa, S.; Hirai, S.; Kasahara, R.; Hariguchi, N.; Matsumoto, M.; Oshima, Y. Exploration of a new type of antimalarial compounds based on febrifugine. J. Med. Chem. 2006, 49, 4698-4706.
6. Briel, D. A new synthesis of pyrido[1,2-a]thieno[3,2-d]pyrimidines. Pharmazie 2003, 58, 836-837.
7. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. 2-Aminothiophenes by the Gewald reaction. J. Heterocycl. Chem. 1999, 36, 333-345.
8. Arnoldi, A.; Dallavalle, S.; Merlini, L.; Musso, L.; Farina, G.; Moretti, M.; Jayasinghe, L. Synthesis and antifungal activity of a series of N-substituted [2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)]propylamines. J. Agric. Food Chem. 2007, 55, 8187-8192.
9. Arnoldi, A.; Carzaniga, R.; Morini, G.; Merlini, L.; Farina, G. Synthesis, fungicidal activity, and QSAR of a series of 2-dichlorophenyl-3- triazolylpropyl ethers. J. Agric. Food Chem. 2000, 48, 2547-2555.
10. Ding, M. W.; Xu, S. Z.; Zhao, J. F. Application of bis(iminophosphorane) in heterocyclic synthesis: New entries to symmetrically or unsymmetrically substituted thieno[2,3-d:5,4-d]dipyrimidine-4,5(3H,6H)-diones. J. Org. Chem. 2004, 69, 8366-8371.
11. Li, H. X.; Xie, C.; Ding, M. W.; Liu, Z. M.; Yang, G. F. Synthesis of a library of imidazolin-4-ones using poly(ethylene glycol) as soluble support. Synlett 2007, 2280-2282.
12. Ding, M. W.; Zeng, G. P.; Liu, Z. J. A regiospecific synthesis of 1-heterocyclic substituted 1,2,4-triazoles via addition reaction of 1,2,4-triazole with functionalized carbodiimide. Synth. Commun. 2002, 32, 3057-3062.
13. Hu, Y. G.; Yang, S. J.; Ding, M. W. Synthesis and fungicidal activities of 2-benzothiazo-lylthio substituted 4H-imidazol-4-ones and 4(3H)- quinazolinones. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1933-1939.
14. Ding, M. W.; Zeng, G. P.; Wu, T. J. A facile synthesis of 2-amino-3H-quinazolin-4-ones with tandem aza-Wittig reaction. Synth. Commun. 2000, 30, 1599-1604.