RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(24): 5371-5379
DOI: 10.1055/s-0036-1591310
DOI: 10.1055/s-0036-1591310
paper
New Efficient Synthesis of 2-Thioxo-2,3-dihydropyrimidin-4(1H)-ones from Baylis–Hillman Adducts
This work was financially supported by the Fundamental Research Funds of Central Universities, Southwest University for Nationalities (No. 13NZYBS05), and the Research projects Sichuan Provincial Department of Education (No. 16ZB0028).Weitere Informationen
Publikationsverlauf
Received: 19. Juli 2017
Accepted after revision: 31. August 2017
Publikationsdatum:
12. Oktober 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201724/lookinside/thumbnails/ss-2017-h0465-op_10-1055_s-0036-1591310-1.jpg)
Abstract
Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes, which reacted with carbon disulfide at 40 °C to produce isothiocyanates. The reaction of these isothiocyanates with primary amines provided thiourea intermediates, which in the presence of potassium carbonate or sodium methoxide were converted into 2-thioxo-2,3-dihydropyrimidin-4(1H)-ones in good yields.
Key words
Baylis–Hillman adducts - iminophosphoranes - isothiocyanates - primary amines - aza-Wittig reaction - 2-thioxo-2,3-dihydropyrimidin-4(1H)-onesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591310.
- Supporting Information
- CIF File
-
References
- 1a Dinakaran VS. Jacob D. Mathew JE. Med. Chem. Res. 2012; 21: 3598
- 1b Yang JJ. Shi DX. Hao PF. Yang DL. Zhang Q. Li JR. Tetrahedron Lett. 2016; 57: 2455
- 1c Macedo D. Mendonça Júnior FJ. B. de Moura RO. Marques-Santos LF. Toxicol. Vitro 2016; 31: 72
- 1d Abbas IM. Gomha SM. Elaasser MM. Mabrouk BK. A. J. Chem. Res. 2015; 719
- 1e Hu YG. Zheng AH. Li GJ. Dong MZ. Ye F. Sun F. Liu ZY. Li W. J. Heterocycl. Chem. 2014; 51: E84
- 2a Lu HH. Xue P. Zhu YY. Ju XL. Zheng XJ. Zhang X. Xiao T. Pannecouque C. Li TT. Gu SX. Bioorg. Med. Chem. 2017; 25: 2491
- 2b Gu SX. Qiao H. Zhu YY. Shu QC. Liu H. Ju XL. De Clercq E. Balzarini J. Pannecouque C. Bioorg. Med. Chem. 2015; 23: 6587
- 2c Yan ZH. Wua HQ. Chen WX. Wu Y. Piao HR. He QQ. Chen FE. De Clercq E. Pannecouque C. Bioorg. Med. Chem. 2014; 22: 3220
- 2d Yu M. Liu X. Li Z. Liu S. Pannecouque C. De Clercq E. Bioorg. Med. Chem. 2009; 17: 7749
- 3a Alam O. Khan SA. Siddiqui N. Ahsan W. Med. Chem. Res. 2010; 19: 1245
- 3b Zhi H. Chen LM. Zhang LL. Liu SJ. Wan DC. C. Lin HQ. Hu C. ARKIVOC 2008; (xiii): 266
- 4a Zeslawska E. Korona-Glowniak I. Szczesio M. Olczak A. Zylewska A. Tejchman W. Malm A. J. Mol. Struct. 2017; 1142: 261
- 4b ElMarrouni A. Heras M. Org. Biomol. Chem. 2015; 13: 851
- 4c Maurya HK. Gupta A. RSC Adv. 2014; 4: 22106
- 4d Taher AT. Helwa AA. Chem. Pharm. Bull. 2012; 60: 521
- 4e Aly HM. Kamal MM. Eur. J. Med. Chem. 2012; 47: 18
- 5 Malothu N. Bhandaru JS. Kulandaivelu U. Jojula M. Adidala RR. Umadevi KR. Dusthackeer AV. N. Kaki VR. Akkinepally RR. Bioorg. Med. Chem. Lett. 2016; 26: 836
- 6a Gomha SM. Ahmed SA. Abdelhamid AO. Molecules 2015; 20: 1357
- 6b Edrees MM. Farghaly TA. El-Hag FA. A. Abdalla MM. Eur. J. Med. Chem. 2010; 45: 5702
- 6c Bosc JJ. Latxague L. Leger JM. Balzarini J. Forfar I. Jarry C. Guillon J. Eur. J. Med. Chem. 2010; 45: 831
- 7a Naidu BN. Sorenson ME. Patel M. Ueda Y. Banville J. Beaulieu F. Bollini S. Dicker IB. Higley H. Lin ZY. Pajor L. Parker DD. Terry BJ. Zheng M. Martel A. Meanwell NA. Krystal M. Walker MA. Bioorg. Med. Chem. Lett. 2015; 25: 717
- 7b Ireland AW. Gobillot TA. Gupta T. Seguin SP. Liang M. Resnick L. Goldberg MT. Manos-Turvey A. Pipas JM. Wipf P. Brodsky JL. Bioorg. Med. Chem. 2014; 22: 6490
- 7c Singh K. Singh K. Balzarini J. Eur. J. Med. Chem. 2013; 67: 428
- 7d Font D. Linden A. Heras M. Villalgordo JM. Tetrahedron 2006; 62: 1433
- 8a Winckelmann I. Larsen EH. Synthesis 1986; 1041
- 8b Alafeefy AM. Ceruso M. Al-Tamimi AM. S. Del Prete S. Capasso C. Supuran CT. Bioorg. Med. Chem. 2014; 22: 5133
- 8c Yestrepsky BD. Kretz CA. Xu YX. Holmes A. Sun HM. Ginsburg D. Larsen SD. Bioorg. Med. Chem. Lett. 2014; 24: 1538
- 8d Laxminarayana B. Kundu LM. Synth. Commun. 2015; 45: 1342
- 8e Hempel JE. Cadar AG. Hong CC. Bioorg. Med. Chem. Lett. 2016; 26: 1947
- 8f Biswas BK. Malpani YR. Ha N. Kwon DH. Shin JS. Kim HS. Kim C. Han SB. Lee CK. Jung YS. Bioorg. Med. Chem. Lett. 2017; 27: 3582
- 9a Basavaiah D. Reddy BS. Badsara SS. Chem. Rev. 2010; 110: 5447
- 9b Basavaiah D. Rao KV. Reddy RJ. Chem. Soc. Rev. 2007; 36: 1581
- 10a Bharadwaj KC. RSC Adv. 2015; 5: 75923
- 10b Wei Y. Shi M. Chem. Rev. 2013; 113: 6659
- 10c Park SP. Song YS. Lee KJ. Tetrahedron 2009; 65: 4703
- 11a Petric MF. Crisan ME. Chumakov YM. Varga RA. Micle A. Neda I. Ilia G. J. Mol. Struct. 2015; 1083: 389
- 11b Cossio FP. Alonso C. Lecea B. Ayerbe M. Rubiales G. Palacios F. J. Org. Chem. 2006; 71: 2839
- 11c Fresneda PM. Molina P. Synlett 2004; 1
- 12a Gololobov YG. Kasukhin LF. Tetrahedron 1992; 48: 1353
- 12b Molina P. Vilaplana MJ. Synthesis 1994; 1197
- 12c Palacios F. Alonso C. Aparicio D. Rubiales G. de los Santos JM. Tetrahedron 2007; 63: 523
- 12d Ashtary M. Ramazani A. Kazemizadeh A. Shajari N. Fattahi N. Joo SW. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 1402
- 13a Khorana HG. Chem. Rev. 1953; 53: 145
- 13b Nishimura Y. Cho H. Synlett 2015; 26: 233
- 13c Wang ZX. Chen LZ. Wang FM. Li B. Han GF. J. Heterocycl. Chem. 2015; 52: 744
- 14 Zimmer H. Singh G. J. Org. Chem. 1963; 28: 483
- 15a Ramazani A. Nasrabadi FZ. Karimi Z. Rouhani M. Synth. Commun. 2013; 43: 1818
- 15b He P. Yan YM. Ding MW. J. Heterocycl. Chem. 2014; 51: E93
- 15c Qu F. Hu RF. Gao L. Wu J. Cheng XH. Wang S. He P. Synthesis 2015; 47: 3701
- 15d Wang HM. Guo SB. Hu YG. Zeng XH. Yang GY. Chin. J. Org. Chem. 2015; 35: 1075
- 15e Ramazani A. Ahmadi Y. Fattahi N. Ahankar H. Pakzad M. Aghahosseini H. Rezaei A. Fardood ST. Joo SW. Phosphorus, Sulfur Silicon Relat. Elem. 2016; 191: 1057
- 15f Nishimura Y. Cho H. Synlett 2015; 26: 233
- 16 Blanco G. Quintela JM. Peinador C. Tetrahedron 2008; 64: 1333
- 17a Yuan D. Kong HH. Ding MW. Tetrahedron 2015; 71: 419
- 17b Xiong J. Wei X. Ding MW. Synlett 2017; 28 1075
- 17c Han EG. Kim HJ. Lee KJ. Tetrahedron 2009; 65: 9616
- 18 Zhong Y. Wu L. Ding MW. Synthesis 2012; 44: 3085
- 19a Zhong Y. Wang L. Ding MW. Tetrahedron 2011; 67: 3714
- 19b Zhong Y. Zhang H. Ding MW. J. Heterocycl. Chem. 2015; 52: 330
- 20 CCDC number 1570136 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.