New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis–Hillman Adducts

Ying Zhong; Lei Wu; Ming-Wu Ding

doi:10.1055/s-0032-1317034

Synthesis, Table of Contents

Synthesis 2012; 44(19): 3085-3089
DOI: 10.1055/s-0032-1317034

paper

New Efficient Synthesis of 2,3,5-Trisubstituted Pyrimidin-4(3H)-ones from Baylis–Hillman Adducts

Ying Zhong

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn

,

Lei Wu

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn

,

Ming-Wu Ding*

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China, Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn

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Abstract

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Abstract

Azides obtained from Baylis–Hillman adducts were treated with triphenylphosphine to give the corresponding iminophosphoranes that underwent aza-Wittig reactions with aryl isocyanates and then reacted with amines, alcohol, or phenols in the presence of catalytic amounts of sodium alkoxide or potassium carbonate to give the corresponding 2,3,5-trisubstituted pyrimidin-4(3H)-ones directly in good yields.

Key words

azides - heterocycles - cyclizations - Wittig reactions - amines - alcohols - phenols

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References

References
1 Zhang Z, Wallace MB, Feng J, Stafford JA, Skene RJ, Shi L, Lee B, Aertgeerts K, Jennings A, Xu R, Kassel DB, Kaldor SW, Navre M, Webb DR, Gwaltney II SL . J. Med. Chem. 2011; 54: 510
2 Dolman NP, Troop HM, More JC. A, Alt A, Knauss JL, Nistico R, Jack S, Morley RM, Bortolotto ZA, Roberts PJ, Bleakman D, Collingridge GL, Jane DE. J. Med. Chem. 2005; 48: 7867
3 Dolman NP, More JC. A, Alt A, Knauss JL, Troop HM, Bleakman D, Collingridge GL, Jane DE. J. Med. Chem. 2006; 49: 2579
4 Gichinga MG, Olson JP, Butala E, Navarro HA, Gilmour BP, Mascarella SW, Carroll FI. ACS Med. Chem. Lett. 2011; 2: 882
5 Zhang J, Zhan P, Wu J, Li Z, Jiang Y, Ge W, Pannecouque C, Clercq ED, Liu X. Bioorg. Med. Chem. 2011; 19: 4366

6a Grosjean S, Triki S, Meslin J.-C, Julienne K, Deniaud D. Tetrahedron 2010; 66: 9912
6b Pierce LT, Cahill MM, McCarthy FO. Tetrahedron 2010; 66: 9754
6c Lu Y, Xiang T, Bartberger MD, Bernard C, Bostick T, Huang L, Liu L, Siegmund A, Sukay G, Guo G, Elipe MS, Tormos W, Dominguez C, Koch K, Burgess LE, Basil TC, Ibrahim P, Hummel C. Tetrahedron 2006; 62: 11714

7a Basavaiah D, Reddy BS, Badsara SS. Chem. Rev. 2010; 110: 5447
7b Declerck V, Martinez J, Lamaty F. Chem. Rev. 2009; 109: 1
7c Singh V, Batra S. Tetrahedron 2008; 64: 4511

8 Pathak R, Madapa S, Batra S. Tetrahedron 2007; 63: 451
9 Lee HS, Kim JM, Kim JN. Tetrahedron Lett. 2007; 48: 4119
10 Sá MM, Fernandes L, Ferreira M, Bortoluzzi AJ. Tetrahedron Lett. 2008; 49: 1228
11 Nayak M, Pandey G, Batra S. Tetrahedron 2011; 67: 7563

12a Naganaboina VK, Chandra KL, Desper J, Rayat S. Org. Lett. 2011; 13: 3718
12b Kshirsagar UA, Puranik VG, Argade NP. J. Org. Chem. 2010; 75: 2702
12c Palacios F, Alonso C, Aparicio D, Rubiales G, de los Santos JM. Tetrahedron 2007; 63: 523
12d Alajarin M, Bonillo B, Ortin M.-M, Sanchez-Andrada P, Vidal A, Orenes R.-A. Org. Biomol. Chem. 2010; 8: 4690
12e Devarie-Baez NO, Xian M. Org. Lett. 2010; 12: 752

13 Liu MG, Hu YG, Ding MW. Tetrahedron 2008; 64: 9052
14 Zhao JF, Xie C, Ding MW, He HW. Synthesis 2005; 2544
15 Ding MW, Xu SZ, Zhao JF. J. Org. Chem. 2004; 69: 8366
16 Huang NY, Liu MG, Ding MW. J. Org. Chem. 2009; 74: 6874
17 Nie YB, Wang L, Ding MW. J. Org. Chem. 2012; 77: 696

18a Yadav JS, Gupta MK, Pandey SK, Reddy BV. S, Sarma AV. S. Tetrahedron Lett. 2005; 46: 2761
18b Sá MM. J. Braz. Chem. Soc. 2003; 14: 1005

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