Full Papers

Sequential One-Pot Synthesis of 5,6,8-Trihydropyrano[3',4':4,5]thieno[2,3-d]pyrimidin-4(3H)-one

  • Chen Li ,
  • Sun Shaofa ,
  • Song Gongwu
Expand
  • a School of Pharmacy, Xianning College, Xianning, Hubei 437100;
    b College of Chemistry and Chemical engineering, Hubei Universit, Wuhan, Hubei 430062

Received date: 2011-11-17

  Revised date: 2012-01-07

  Online published: 2012-03-05

Supported by

Project supported by the Natural Science Foundation of Hubei Province (No. 2010CDZ048).

Abstract

Nineteen novel 5,6,8-trihydropyrano [3',4':4,5] thieno [2,3-d] pyrimidin-4(3H)-one derivatives were synthsized using the sequential one-pot reaction, from 4,5,7-trihydropyrano [4,3-d] thiophen-2-ylimino-triphenyl-phosohorane, aryl-isocyanate and primary amine or secondary amine. Their structures were characterized by 1H NMR, IR and MS. Meanwhile, the structure of 3-(4-chlorophenyl)-2-(diethylamino)-5,6,8-trihydropyrano [3',4':4,5] thieno [2,3-d] pyrimidin-4(3H)-one (4a) was further confirmed by X-ray single diffraction method.

Cite this article

Chen Li , Sun Shaofa , Song Gongwu . Sequential One-Pot Synthesis of 5,6,8-Trihydropyrano[3',4':4,5]thieno[2,3-d]pyrimidin-4(3H)-one[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1314 -1318 . DOI: DOI: 10.6023/cjoc1111172

References

1 Rashad, A. E.; Shamroukh, A. H.; Abdel-Megeid, R. E.; El-Sayed, W. A. Syn. Comm. 2010, 40, 1149.  
2 Shetty, N. S.; Lamani, R. S.;Khazi, I. A. M. J. Chem. Sci. 2009, 121, 301.  
3 Castro, A.; Jerez, M. J.; Gil, C.; Calderon, F.; Dome′nech, T.; Nueda, A.; Martnez, A. Eur. J. Med. Chem. 2008, 43, 1349. (曾国平, 段连生, 丁明武. 华中师范大学学报(自然科学版), 2008, 42, 58  
4 Carpenter, A. J.; Al-Barazanji, K. A.; Barvian, K. K.; Bishop, M. J.; Britt, C. S.; Cooper, J. P.; Goetz, A. S.; Grizzle, M. K.; Hertzog, D. L.; Ignr, D. M.; Morgan, R. O.; Peckham, G. E.; Speake, J. D.; Swain, W. R. Bioorg. Med. Chem. Lett. 2006, 16, 4994.  
5 Hertzog, D. L.; Witty, D. R. Curr. Top. Med. Chem. 2007, 7, 1455.  
6 Alagarsamya, V.; Meenab, S.; Ramseshu, K. V.; Solomon, V. R.; Thirumurugan, K.; Dhanabal, K.; Murugana, M. Eur. J. Med. Chem. 2006, 41, 1293.  
7 Crespo, M. I.; Pages, L.; Vega, A.;Segarra, V.;Lopez,M.; Domenech, T.; Miralpeix, M.; Beleta, J.; Ryder, H.; Palacios, J. M. J. Med. Chem. 1998, 41, 4021.  
8 Ivachtchenko, A.; Kovalenko, S.; Tkachenko, O. V.; Parkhomenko, O. J. Comb. Chem. 2004,6,573.  
9 Vovk, M. V.; Bolbut, A. V.; Boiko, V. I.; Pirozhenko, V. V; Chemega, A. N.; Tolmachev, A. A. Chem. Heterocycl. Comp. 2004, 40, 370.  
10 Mohan, C.; Kumar, V.; Mahajan, M. P. Terahedron, 2005, 61, 10774.  
11 Fang, Z.-D. M.S. Thesis, Central China Normal University, Wuhan,2006 (in Chinese) (方正东, 硕士论文, 华中师范大学, 武汉, 2006)
12 Hu, Y.-G.; Lu, M.-Y.; Song, H.-L.; Ding, M.-W. Chin. J. Org. Chem. 2005, 25, 295 (in Chinese) (胡杨根, 吕茂云, 宋鹤丽, 丁明武. 有机化学. 2005, 25, 295)
13 Zeng, G.-P.; Duan, L.-S.; Ding, M.-W. Journal of Huazhong Normal University (Nat.Sci.), 2008, 42, 58 (in Chinese)
Outlines

/