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Synthesis 2013; 45(22): 3164-3172
DOI: 10.1055/s-0033-1338533
DOI: 10.1055/s-0033-1338533
paper
Iron(III) Chloride Catalyzed Synthesis of Functionalized Spiropyrimidines
Further Information
Publication History
Received: 31 May 2013
Accepted after revision: 22 August 2013
Publication Date:
24 September 2013 (online)
Abstract
Potentially bioactive pyrimidine-annulated spiroheterocyclic compounds are synthesized in good to excellent yields using readily available, cheap and environmentally friendly iron(III) chloride (FeCl3) as the catalyst. The process is straightforward and provides a diverse range of spiropyrimidine derivatives via the 5-endo-dig mode of cyclization, starting from simple and easily available starting materials.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Mead KT, Brewer BN. Curr. Org. Chem. 2003; 7: 227
- 2 Shi Z.-J, Zhang S.-L, Cao W.-G, Deng H.-M. Chin. J. Chem. 2008; 26: 2103-2106 ; Molbank 2012, M773, 4
- 3 Yang L, Qin L.-H, Bligh SW. A, Bashall A, Zhang C.-F, Zhang M, Wang Z.-T, Xu L.-S. Bioorg. Med. Chem. 2006; 14: 3496
- 4 Gates PS, Baldwin D, Wilson CA, Gillon J. US Patent 4263037, 1982 ; Chem. Abstr. 1982, 97, 215978.
- 5 Edwards PN, Large MS. EP Patent 316079, 1989 ; Chem. Abstr. 1989, 111, 232794.
- 6 Chan AS. C, Lin CC, Sun J, Hu W, Li Z, Pan W, Mi A, Jiang Y, Huang TM, Yang TK, Chen JH, Wang Y, Lee GH. Tetrahedron: Asymmetry 1995; 6: 2953
- 7 Fu Y, Xie J.-H, Hu A.-G, Zhou H, Wang L.-X, Zhou Q.-L. Chem. Commun. 2002; 480
- 8a Hu A.-G, Fu Y, Xie J.-H, Zhou H, Wang L.-X, Zhou Q.-L. Angew. Chem. Int. Ed. 2002; 41: 2348
- 8b Amutha P, Nagarajan S. Helv. Chim. Acta 2010; 93: 430
- 8c Gozalishvili LL, Beryozkina TV, Omelchenko IV, Zubatyuk RI, Shishkin OV, Kolos NN. Tetrahedron 2008; 64: 8759
- 8d Dandia A, Jain AK, Sharma S. RSC Adv. 2013; 3: 2924
- 8e Kanawade SB, Patil SP, Nikam PS, Gangurde SA, Jachak MN, Toche RB. J. Heterocycl. Chem. 2012; 49: 363
- 9a Nieczypor P, Mol JC, Bespalova NB, Bubnov YN. Eur. J. Org. Chem. 2004; 812
- 9b Krasnov KA, Kartsev VG. Chem. Nat. Compd. 2011; 46: 915
- 10a Lunt E In Comprehensive Organic Chemistry . Vol. 4. Barton D, Ollis WD. Pergamon Press; Oxford: 1974: 493
- 10b Sasaki T, Minamoto K, Sujuki T, Yamashita S. Tetrahedron 1980; 36: 865
- 10c Bradshaw TK, Hutchinson DW. Chem. Soc. Rev. 1977; 6: 43
- 11a Marumoto R, Furukawa Y. Chem. Pharm. Bull. 1977; 25: 2974
- 11b Cheng CC, Roth B. Prog. Med. Chem. 1971; 8: 61
- 11c Jones SA, Sayers JR, Walker RT, De Clercq E. J. Med. Chem. 1988; 31: 268
- 12a Macilwain C. Nature 1993; 365: 378
- 12b Balzarini J, Pauwels R, Hardewijn P, Clercq ED, Cooney DA, Kanj GJ, Dalai M, Jones DG, Breder S. Biochem. Biophys. Res. Commun. 1986; 140: 735
- 13a Mangiavacchi S, Calistri MT. Ann. Chim. 1973; 63: 883
- 13b Wolf M, Diebold JL. US Patent 3714093, 1973 ; Chem. Abstr. 1973, 78, 111344.
- 13c Mamaev VP, Borovik VP, Gorfinkel MI, Ivanovskaya LYu. Izv. Akad. Nauk SSSR, Ser. Khim. 1970; 7: 1637
- 14a Majumdar KC, Ghosh T, Shyam PK. Synlett 2011; 2657
- 14b Majumdar KC, Ganai S, Nandi RK. New J. Chem. 2011; 35: 1355
- 15a Majumdar KC, Taher A, Ponra S. Tetrahedron Lett. 2010; 51: 2297
- 15b Majumdar KC, Taher A, Ponra S. Tetrahedron Lett. 2010; 51: 147
- 15c Majumdar KC, Taher A, Ponra S. Synlett 2010; 735
- 15d Majumdar KC, Ray K, Ponra S. Tetrahedron Lett. 2010; 51: 5437
- 15e Majumdar KC, Taher A, Ponra S. Synthesis 2010; 4043
- 15f Majumdar KC, Ponra S, Ganai S. Synlett 2010; 2575
- 15g Majumdar KC, Ponra S, Ghosh D, Taher A. Synlett 2011; 104
- 15h Majumdar KC, Ponra S, Ghosh D. Synthesis 2011; 1132
- 15i Majumdar KC, Taher A, Ponra S. Synthesis 2011; 3716
- 15j Majumdar KC, Ponra S, Nandi RK. Eur. J. Org. Chem. 2011; 6909
- 15k Majumdar KC, Ponra S, Ghosh T. RSC Adv. 2012; 2: 1144
- 15l Majumdar KC, Ponra S, Ghosh T. Synthesis 2012; 44: 2079
- 15m Majumdar KC, Ponra S, Nandi RK. Tetrahedron Lett. 2012; 53: 1732
- 16a Correa A, Mancheno OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
- 16b Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
- 16c Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
- 16d Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
- 16e Diaz DD, Miranda PO, Padron JI, Martín VS. Curr. Org. Chem. 2006; 10: 457
- 17 Khadilker BM, Borkar SD. Tetrahedron Lett. 1997; 38: 1641
- 18 Yang H, Li B, Cui Y. Synth. Commun. 1998; 28: 1233
- 19 Chatterjee SK, Nuhn P. Chem. Commun. 1998; 1729
- 20 Kuroda C, Koshio H. Chem. Lett. 2000; 962
- 21 Roy B, Ansary I, Samanta S, Majumdar KC. Tetrahedron Lett. 2012; 53: 5119
- 22 Yeh M.-CP, Fang C.-W, Lin H.-H. Org. Lett. 2012; 14: 1830