Efficient synthesis of thieno[2,3-d]pyrimidin-4(3H)-ones by a sequential aza-Wittig reaction/base catalyzed cyclization

Heterocyclic Communications

Volumn 17, Issue 5-6, 2011, Pages 197-201

  Dai, Zhong Xu ^a   Chen, Hong ^a   Liu, Ming Guo ^a   Ding, Ming Wu ^b  

^a CHINA THREE GORGES UNIVERSITY   (China)

^b CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

3 d pyrimidin 4(3H) one; Aza Wittig reaction; Carbodiimide; Iminophosphorane; Thieno 2

Indexed keywords

EID: 84862975372     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2011.049     Document Type: Article

References (24)

1. Amr, A. E. G.; Sherif, M. H.; Assy, M. G.; Al-Omar, M. A.; Ragab, I. Antiarrhythmic, serotonin antagonist and antianxiety activities of novel substituted thiophene derivatives synthesized from 2-amino-4,5,6,7-tetrahydro-N- phenylbenzo[b]thiophene-3-carboxamide. Eur. J. Med. Chem. 2010, 45, 5935-5942.
2. Blanco, G.; Segui, N.; Quintela, J. M.; Peinador, C.; Chas, M.; Toba, R. A practical one-pot procedure for the synthesis of pyrazino[2',3' :4,5]thieno[3,2-d]pyrimidinones by a tandem aza-Wittig/heterocumulene-mediated annulation strategy. Tetrahedron 2006, 62, 11124-11135. (Pubitemid 44573337)
3. Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 2005, 44, 5188-5240. (Pubitemid 41223873)
4. Ding, M. W. The Wittig Reaction in the Heterocyclic Synthesis; Central China Normal University Press: Wuhan, 1997, pp. 73-74.
5. Ding, M. W.; Sun, Y.; Liu, X. P.; Liu, Z. J. A new solution-phase parallel synthesis of 2-alkylamino-3-aryl-5-phenylmethylene-3,5-dihydro-4 H-imidazol-4-ones. Chin. J. Chem. 2003, 21, 577-580.
6. Ding, M. W.; Chen, Y. F.; Huang, N. Y. New efficient synthesis of 1,2,4-triazolo[5,1-b]quinazolin-9(3 H)-ones via a tandem aza-Wittig/ heterocumulene-mediated annulation. Eur. J. Org. Chem. 2004, 18, 3872-3878.
7. Ding, M. W.; Xu, R. J.; Chen, Y. F. A selective synthesis of 2-alkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4-(3 H)-ones. Chin. Chem. Lett. 2005, 16, 189-192.
8. He, P.; Wu, J.; Nie, Y. B.; Ding, M. W. New efficient synthesis of 4-aminocarbonyl substituted 4 H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence. Tetrahedron 2009, 65, 8563-8570.
9. Huang, N. Y.; Liu, M. G.; Ding, M. W. Efficient regioselective synthesis of indole N-carboximidamides and N-carboximidoates by a sequential aza-Wittig/Ag(I)-catalyzed cyclization. J. Org. Chem. 2009, 74, 6874-6877.
10. Jennings, L. D.; Kincaid, S. L.; Wang, Y. D. Parallel synthesis and biological evaluation of 5,6,7,8-tetrahydrobenzothieno[2,3-d] pyrimidin-4(3 H)-one cytotoxic agents selective for p21-deficient cells. Bioorg. Med. Chem. Lett. 2005, 15, 4731-4735. (Pubitemid 41354796)
11. Lertpibulpanya, D.; Marsden, S. P.; Rodriguez-Garcia, I.; Kilner, C. A. Asymmetric Aza-Wittig reactions: enantioselective synthesis of β-quaternary azacycles. Angew. Chem. Int. Ed. 2006, 45, 5000-5002. (Pubitemid 44166141)
12. 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, 14, 2280-2282. (Pubitemid 47439772)
13. Liang, Y.; Ding, M. W.; Liu, Z. J.; Liu, X. P. A facile and selective synthesis of 2-alkylamino-4(3H)-quinazolinones. Synth. Commun. 2003, 33, 2843-2848. (Pubitemid 36951537)
14. Mavrova, A. T.; Vuchev, D.; Anichina, K.; Vassilev, N. Synthesis, antitrichinnellosis and antiprotozoal activity of some novel thieno[2,3-d]pyrimidin-4(3 H)-ones containing benzimidazole ring. Eur. J. Med. Chem. 2010, 45, 5856-5861.
15. Modica, M.; Santagati, M.; Russo, F. High affinity and selectivity of [[(arylpiperazinyl)alkyl]thio]thieno[2,3-d]pyrimidinone derivatives for the 5-HT 1A receptor. Synthesis and structure-affinity relationships. Eur. J. Med. Chem. 2000, 35, 677-689. (Pubitemid 30490274)
16. Modica, M.; Santagati, M.; Guccione, S. Design, synthesis and binding properties of novel and selective 5-HT3 and 5-HT4 receptor ligands. Eur. J. Med. Chem. 2001, 36, 287-301. (Pubitemid 32406203)
17. Nakanishi, M.; Tahara, T. U. S. Patent 3,563,997, February 16, 1971.
18. Palacios, F.; Alonso, C.; Aparicio, D.; Rbbiales, G.; Santos, J. M. The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds. Tetrahedron 2007, 63, 523-575. (Pubitemid 44881045)
19. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. 2-Aminothiophenes by the Gewald reaction. J. Heterocyclic Chem. 1999, 36, 333-345. (Pubitemid 29220939)
20. Wang, Y. D.; Johnson, S.; Powell, D. Inhibition of tumor cell proliferation by thieno[2,3-d]pyrimidin-4(1 H)-one-based analogs. Bioorg. Med. Chem. Lett. 2005, 15, 3763-3766. (Pubitemid 41038974)
21. Warshakoon, N. C.; Sheville, J.; Bhatt, R. T. Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents. Bioorg. Med. Chem. Lett. 2006, 16, 5207-5211. (Pubitemid 44247686)
22. Witty, D. R.; Bateson, J.; Hervieu, G. J. Discovery of potent and stable conformationally constrained analogues of the MCH R1 antagonist SB-568849. Bioorg. Med. Chem. Lett. 2006, 16, 4872-4878. (Pubitemid 44177776)
23. Yuan, J. Z.; Fu, B. Q.; Ding, M. W.; Yang, G. F. New facile synthesis of 3,5-dihydro-6 H-imidazo[1,2-b]-1,2,4-triazol-6-ones by an iminophosphorane- mediated annulation. Eur. J. Org. Chem. 2006, 18, 4170-4174.
24. Zhang, M. Z.; Tamiya, J.; Nguyen, L. Thienopyrimidinone- bisaminopyrrolidine ureas as potent melanin concentrating hormone receptor-1 (MCH-R1) antagonists. Bioorg. Med. Chem. Lett. 2007, 17, 2535-2539. (Pubitemid 46507778)