Synthesis of Dihydropyrimidinones
and Thiones by Multicomponent Reactions: Strategies Beyond
the Classical Biginelli Reaction

Jie-Ping Wan; Yunyun Liu

doi:10.1055/s-0030-1258290

REVIEW

Synthesis of Dihydropyrimidinones and Thiones by Multicomponent Reactions: Strategies Beyond the Classical Biginelli Reaction

Jie-Ping Wan*, Yunyun Liu
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China
Fax: +86(791)8120380; e-Mail: wanjieping@gmail.com;

Abstract

Alle Artikel dieser Rubrik

Abstract

The three-component Biginelli reaction for the synthesis of dihydropyrimidinone and corresponding dihydropyrimidinethiones (DHPMs) has been known for more than a century. Consistent attention has been paid to the study of Biginelli reaction owing to the significant biological and pharmaceutical merits of DHPMs. In the view of molecular diversity, the development of new multicomponent reactions that provide DHPMs bearing novel functional structures has emerged as a central issue in recent years. This account systematically summarizes the multicomponent reaction syntheses of novel DHPMs that are not accessible through the classical Biginelli reaction.

1 Introduction

2 Synthesis of DHPMs via Modification of Classical Biginelli Substrates

2.1 Using β-Keto Ester Alternatives

2.2 Using Urea/Thiourea Alternatives

2.3 Using Aldehyde Alternatives

3 Synthesis of DHPMs via Other Multicomponent Reactions

4 Conclusions

Key words

dihydropyrimidinone - dihydropyrimidinethione - multicomponent reactions

Volltext

Referenzen

Reference

1 Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3168

2 Dömling A. Chem. Rev. 2006, 106: 17

3 Multicomponent Reactions Zhu J. Bienayme H. Wiley-VCH; Weinheim: 2005.

4 Ganem B. Acc. Chem. Res. 2009, 42: 463

5 Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res. 2003, 36: 899

6 Ulaczyk-Lesanko A. Hall DG. Curr. Opin. Chem. Biol. 2005, 9: 226

7 Edraki N. Mehdipour AR. Khoshneviszadeh M. Miri R. Drug Discovery Today 2009, 14: 1058

8 Tietze LF. Lieb ME. Curr. Opin. Chem. Biol. 1998, 2: 363

9 Biginelli P. Gazz. Chim. Ital. 1893, 23: 360

10 Mayer TM. Kapoor TM. Haggarty SJ. King RW. Schreiber SL. Mitchison TJ. Science 1999, 286: 971

11 Garcia-Saez I. DeBonis S. Lopez R. Trucco F. Rousseau B. Thuéry P. Kozielski F. J. Biol. Chem. 2007, 282: 9740

12 Atwal KS. Swanson BN. Unger SE. Floyd DM. Moreland S. Hedberg A. O’Reilly BC. J. Med. Chem. 1991, 34: 806

13 Kappe CO. Eur. J. Med. Chem. 2000, 35: 1043

14 Singh K. Arora D. Singh K. Singh S. Mini-Rev. Med. Chem. 2009, 1: 95

15 Kim SS. Choi BS. Lee JH. Lee KK. Lee TH. Kim YH. Hyunik S. Synlett 2009, 599

16 Yamamoto K. Chen YG. Buono FG. Org. Lett. 2005, 7: 4573

17 Wang X.-C. Quan Z.-J. Zhang Z. Tetrahedron 2007, 63: 8227

18 Wang X.-C. Quan Z.-J. Zhang Z. Liu Y.-J. Ji P.-Y. Lett. Org. Chem. 2007, 4: 370

19 Pérez R. Beryozkina T. Zbruyev OI. Haas W. Kappe CO. J. Comb. Chem. 2004, 4: 501

20 Lengar A. Kappe CO. Org. Lett. 2004, 6: 771

21 Chanetskyy B. Dallinger D. Kappe CO. J. Comb. Chem. 2004, 6: 884

22 Kappe CO. Tetrahedron 1993, 49: 6937

23 Kappe CO. Acc. Chem. Res. 2000, 33: 879

24 Kappe CO. Stadler A. Org. React. 2004, 63: 1

25 For a review of enantioselective synthesis of DHPMs via the Biginelli reaction, see: Gong L.-Z. Chen X.-H. Xu X.-Y. Chem. Eur. J. 2007, 13: 8920

26 Bussolari JC. McDonnell PA. J. Org. Chem. 2000, 65: 6777

27 Abelman MM. Smith SC. James DR. Tetrahedron Lett. 2003, 44: 4559

28a Wang Z.-T. Xu L.-W. Xia C.-G. Wang H.-Q. Tetrahedron Lett. 2004, 45: 7951

28b Wang Z.-T. Xu L.-W. Xia C.-G. Wang H.-Q. Tetrahedron Lett. 2006, 47: 1361

29 Sabitha G. Reddy KB. Srinivas R. Yadav JS. Helv. Chim. Acta 2005, 88: 2996

30 Liang B. Wang X. Wang J.-X. Du Z. Tetrahedron 2007, 63: 1981

31 Ren Y.-M. Cai C. Monatsh. Chem. 2009, 140: 49

32 Kefayati H. Fakhriyannejad M. Mohammadi AA. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184: 1796

33 Zhu Y.-L. Huang S.-L. Pan Y.-J. Eur. J. Org. Chem. 2005, 2354

34 Zhang H. Zhou Z. Yao Z. Xu F. Shen Q. Tetrahedron Lett. 2009, 50: 1622

35 Hong M. Cai C. J. Heterocycl. Chem. 2009, 46: 1430

36 Figueroa-Valverde L. Díaz-Cedillo F. Camacho-Luis A. Monatsh. Chem. 2010, 141: 75

37 Pisani L. Prokopcová H. Kremsner MK. Kappe CO. J. Comb. Chem. 2007, 9: 415

38 Prokopcová H. Pisani L. Kappe CO. Synlett 2007, 43

39 Stadler A. Kappe CO. J. Comb. Chem. 2001, 3: 624

40 Schmidt TJ. Lombardo LJ. Traeger SC. Williams DK. Tetrahedron Lett. 2008, 49: 3009

41 Kumar BRP. Sankar G. Biag RBN. Chandrashekaran S. Eur. J. Med. Chem. 2009, 42: 4192

42a Lombardo L, and Wu L. inventors; U.S. Patent 6,809,102.

42b Lombardo L, and Wu L. inventors; U.S. Patent 6,900,214.

43 Savant MM. Pansuriya AM. Bhuva CV. Kapuriya NP. Naniapara YT. Catal. Lett. 2009, 132: 281

44 Singh OM. Devi NS. J. Org. Chem. 2009, 74: 3141

45 Bailey CD. Houlden CE. Bar GLJ. Lloyd-Jones GC. Booker-Milburn KI. Chem. Commun. 2007, 2932

46 Wan J.-P. Pan Y.-J. Chem. Commun. 2009, 2768

47 Vanden Eynde JJ. Hecq N. Kataeva O. Kappe CO. Tetrahedron 2001, 57: 1785

48 Aron ZD. Overman LE. Chem. Commun. 2004, 253

49 Chebanov VA. Muravyova EA. Desenko SM. Musatov VI. Knyazeva IV. Shishkina SV. Shishkin OV. Kappe CO. J. Comb. Chem. 2006, 8: 427

50 Gladkov ES. Chebanov VA. Desenko SM. Shishkin OV. Shishkina SV. Dallinger D. Kappe CO. Heterocycles 2007, 73: 469

51 Yao C. Lei S. Wang C. Yu C. Tu S. J. Heterocycl. Chem. 2008, 45: 1609

52 Zheng L.-Y. Cai C. J. Comb. Chem. 2010, 12: 35

53 Chen Q. Jiang L.-L. Chen C.-N. Yang G.-F. J. Heterocycl. Chem. 2009, 46: 139

54 Hulme R. Zamora ODP. Mota EJ. Pastén MA. Contreras-Rojas R. Miranda R. Valencia-Hernández I. Correa-Basurto J. Trujillo-Ferrara J. Delgade F. Tetrahedron 2008, 64: 3372

55 Ryabukhin SV. Plaskon AS. Ostapchuk EN. Volochnyuk DM. Tolmachev AA. Synthesis 2007, 417

56 Arjun M. Sridhar D. Chari MA. Sarangapani M. J. Heterocycl. Chem. 2009, 46: 119

57 Folkers K. Johnson TB. J. Am. Chem. Soc. 1933, 55: 3784

58 Sweet F. Fissekis JD. J. Am. Chem. Soc. 1973, 95: 8741

59 Kappe CO. J. Org. Chem. 1997, 62: 7201

60a Dondoni A. Massi A. Minghini E. Sabbatini S. Bertolasi V. J. Org. Chem. 2003, 68: 6172

60b

See also related references in Kappe’s review (ref. 14).

61 Csámpai A. Györfi AZ. Túrós GI. Sohár P. J. Organomet. Chem. 2009, 694: 3667

62 Singh K. Singh J. Deb PK. Singh H. Tetrahedron 1999, 55: 12873

63 Khosropour AR. Khodaei MM. Beygzadeh M. Jokar M. Heterocycles 2005, 65: 767

64 Khodaei MM. Khosropour AR. Jowkar M. Synthesis 2005, 1301

65 Vugts DJ. Jansen H. Schmitz RF. de Kanter FJJ. Orru RVA. Chem. Commun. 2003, 2594

66 Zhu J. Zhang MJ. Liu B. Li X. Chem. Lett. 2009, 38: 56

67 Shaabani A. Seyyedhamzeh M. Maleki A. Hajishaaban-ha F. Tetrahedron 2010, 66: 4040