Abstract
A regio- and stereoselective synthesis of functionalized 4,5-disubstituted oxazolidin-2-ones is reported with moderate to good yields from the reaction of α-epoxyketones with urea in the presence of p-toluenesulfonic acid as the catalyst.
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GK Friestad J Qin (2000) J Am Chem Soc 122 8329 Occurrence Handle10.1021/ja002173u Occurrence Handle1:CAS:528:DC%2BD3cXlsFKntbc%3D
SD Bull SG Davies RL Nicholson HJ Sanganee AD Smith (2000) Tetrahedron: Asymmetry 11 3475 Occurrence Handle10.1016/S0957-4166(00)00333-5 Occurrence Handle1:CAS:528:DC%2BD3cXosVGjt70%3D
P Bravo S Fustero M Guidetti A Volonterio M Zanda (1999) J Org Chem 64 8731 Occurrence Handle10.1021/jo9909397 Occurrence Handle1:CAS:528:DyaK1MXnt1ShtL4%3D
SD Bull SG Davies S Jones HJ Sanganee (1999) J Chem Soc Perkin Trans 1 387 Occurrence Handle10.1039/a809715a
SG Davies HJ Sanganee P Szolcsanyi (1999) Tetrahedron 55 3337 Occurrence Handle10.1016/S0040-4020(98)01145-4 Occurrence Handle1:CAS:528:DyaK1MXhslyjur4%3D
Reddy GV, Rao GV, Iyengar DS (1999) Chem Commun:317
DJ Ager I Prakash DR Schaad (1996) Chem Rev 96 835 Occurrence Handle10.1021/cr9500038 Occurrence Handle1:CAS:528:DyaK28XhsVGhtrc%3D
M Takhi C Murugan M Munikumar KM Bhaskarreddy G Singh K Sreenivas M Sitaramkumar N Selvakumar J Das S Trehan J Iqbal (2006) Bioorg Med Chem Lett 16 2391 Occurrence Handle10.1016/j.bmcl.2006.01.109 Occurrence Handle1:CAS:528:DC%2BD28XislChu78%3D
G Wang JR Ella-Menye V Sharma (2006) Bioorg Med Chem Lett 16 2177 Occurrence Handle10.1016/j.bmcl.2006.01.072 Occurrence Handle1:CAS:528:DC%2BD28XitlartLk%3D
N Selvakumar GS Kumar AM Azhagan GG Rajulu S Sharma MS Kumar J Das J Iqbal S Trehan (2007) Eur J Med Chem 42 538 Occurrence Handle10.1016/j.ejmech.2006.10.013 Occurrence Handle1:CAS:528:DC%2BD2sXktVensb8%3D
KS Jandu V Barrett M Brockwell D Cambridge DR Farrant C Foster H Giles RC Glen AP Hill H Hobbs A Honey GR Martin J Salmon D Smith P Woollard DL Selwood (2001) J Med Chem 44 681 Occurrence Handle10.1021/jm000956k Occurrence Handle1:CAS:528:DC%2BD3MXlsFygtw%3D%3D
JM Liu XG Peng JH Liu SZ Zheng W Sun CG Xia (2007) Tetrahedron Lett 48 929 Occurrence Handle10.1016/j.tetlet.2006.12.028 Occurrence Handle1:CAS:528:DC%2BD2sXnvFGgsQ%3D%3D
A Hamdach RJ Zaragozá E Zaballos-García J Sepúlveda-Arques (2007) J Mol Struc: THEOCHEM 806 141 Occurrence Handle10.1016/j.theochem.2006.11.026 Occurrence Handle1:CAS:528:DC%2BD2sXhsFKms7k%3D
E Boyd S Chavda E Coulbeck GS Coumbarides M Dingjan J Eames A Flinn AK Krishnamurthy M Namutebi J Northen Y Yohannes (2006) Tetrahedron: Asymmetry 17 3406 Occurrence Handle10.1016/j.tetasy.2007.01.003 Occurrence Handle1:CAS:528:DC%2BD2sXht12qur4%3D
JE Hein LM Geary AA Jaworski PG Hultin (2005) J Org Chem 70 9940 Occurrence Handle10.1021/jo051696n Occurrence Handle1:CAS:528:DC%2BD2MXhtFalu7jO
M Ciclosi C Fava R Galeazzi M Orena ME Gonzalez-Rosende J Sepúlveda-Arques (2004) Tetrahedron: Asymmetry 15 1937 Occurrence Handle10.1016/j.tetasy.2004.05.006 Occurrence Handle1:CAS:528:DC%2BD2cXkvFymsbc%3D
CS Park MS Kim TB Sim DK Pyun CH Lee D Choi WK Lee (2003) J Org Chem 68 43 Occurrence Handle10.1021/jo025545l Occurrence Handle1:CAS:528:DC%2BD38Xjs1GgtL4%3D
F Coelho RC Rossi (2002) Tetrahedron Lett 43 2797 Occurrence Handle10.1016/S0040-4039(02)00351-9 Occurrence Handle1:CAS:528:DC%2BD38XisFGksb4%3D
M Feroci A Gennaro A Inesi M Orsini L Palomb (2002) Tetrahedron Lett 43 5863 Occurrence Handle10.1016/S0040-4039(02)01186-3 Occurrence Handle1:CAS:528:DC%2BD38Xls1Gktbs%3D
A Hamdach EM El-Hadrami S Gil RJ Zaragozá E Zaballos-Garcí J Sepúlveda-Arques (2006) Tetrahedron 62 6392 Occurrence Handle10.1016/j.tet.2006.04.033 Occurrence Handle1:CAS:528:DC%2BD28Xlt12ntbw%3D
E Boyd S Chavda E Coulbeck GS Coumbarides M Dingjan J Eames A Flinn AK Krishnamurthy M Namutebi J Northen Y Yohannes (2006) Tetrahedron: Asymmetry 17 3406 Occurrence Handle10.1016/j.tetasy.2007.01.003 Occurrence Handle1:CAS:528:DC%2BD2sXht12qur4%3D
R Green PJM Taylor SD Bull TD James MF Mahon AT Merritt (2003) Tetrahedron: Asymmetry 14 2619 Occurrence Handle10.1016/S0957-4166(03)00482-8 Occurrence Handle1:CAS:528:DC%2BD3sXmvV2ls7o%3D
MR Banks JIG Cadogan I Gosney RO Gould PKG Hodgson D McDougall (1998) Tetrahedron 54 9765 Occurrence Handle10.1016/S0040-4020(98)00531-6 Occurrence Handle1:CAS:528:DyaK1cXltFeitr8%3D
TR Abbas JIG Cadogan AA Doyle I Gosney PKG Hodgson GE Howells AM Hulme S Parsons IH Sadler (1997) Tetrahedron Lett 38 4917 Occurrence Handle10.1016/S0040-4039(97)01058-7 Occurrence Handle1:CAS:528:DyaK2sXksFSkuro%3D
JIG Cadogan AA Doyle I Gosney PKG Hodgson P Thorburn (1997) Enantiomer 2 81 Occurrence Handle1:CAS:528:DyaK2sXlt1Wns7Y%3D
Huth A, Frost E (1983) Liebigs Ann Chem:261
HR Memarian F Nikpour (2002) Monatsh Chem 133 1045 Occurrence Handle10.1007/s007060200038 Occurrence Handle1:CAS:528:DC%2BD38Xmtlemsbw%3D
HR Memarian F Nikpour (2002) Molecules 7 63 Occurrence Handle1:CAS:528:DC%2BD38Xhsl2ktrg%3D Occurrence Handle10.3390/70100063
GB Payne (1959) J Am Chem Soc 81 4901 Occurrence Handle10.1021/ja01527a035 Occurrence Handle1:CAS:528:DyaF3cXnsVGltg%3D%3D
GB Payne (1959) J Org Chem 24 2048 Occurrence Handle10.1021/jo01094a623 Occurrence Handle1:CAS:528:DyaF3cXlsF2ksg%3D%3D
CV Kumar D Ramaiah PK Das MV Georg (1985) J Org Chem 50 2818 Occurrence Handle10.1021/jo00216a003 Occurrence Handle1:CAS:528:DyaL2MXkslSks7k%3D
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Correspondence: Farzad Nikpour, Department of Chemistry, Faculty of Sciences, University of Kurdistan, P.O. Box 66315-416, Sanandaj, Iran.
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Nikpour, F., Mohebbi, S., Paibast, T. et al. Regio- and stereoselective synthesis of functionalized oxazolidin-2-ones from the reaction of α-epoxyketones with urea. Monatsh Chem 139, 663–667 (2008). https://doi.org/10.1007/s00706-007-0820-1
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DOI: https://doi.org/10.1007/s00706-007-0820-1