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Synthesis 2007(12): 1779-1784
DOI: 10.1055/s-2007-983714
DOI: 10.1055/s-2007-983714
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Novel Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazolines by the Regioselective Cyclization of 1,4-Disubstituted Thiosemicarbazides
Further Information
Received
31 January 2007
Publication Date:
08 June 2007 (online)
Publication History
Publication Date:
08 June 2007 (online)
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Abstract
A novel and efficient route for the regioselective synthesis of 5-aryl-2-[(4-aryl-2-oxo-1,3,2-dioxaphosphinan-2-yl)imino]-2,3-dihydro-1,3,4-oxadiazoles in high yield and purity by the desulfurization and cyclization of 1-benzoyl-4-[(4-aryl-2-oxo-1,3,2-dioxaphosphinan-2-yl)thiosemicarbazides under mild conditions is reported. The products are isolated as the trans-isomer only.
Key words
oxadiazole - thiosemicarbazide - regioselective - cyclization - desulfurization
-
1a
Wu MT. J. Heterocycl. Chem. 1972, 9: 31 -
1b
Kress TJ.Costantino SM. J. Heterocycl. Chem. 1980, 17: 607 -
1c
Yale HL.Losee K. J. Med. Chem. 1966, 9: 478 -
2a
Ainsworth C.Jones RG. J. Am. Chem. Soc. 1953, 75: 4915 -
2b
Campaigne E.Selby TP. J. Heterocycl. Chem. 1978, 15: 401 -
2c
Okawara T.Tateyama Y. J. Heterocycl. Chem. 1988, 25: 1071 -
2d
Sung KS.Lee AR. J. Heterocycl. Chem. 1992, 29: 1101 -
2e
Wang ZY.Shi HJ.Shi HX. Youji Huaxue 1997, 17: 271 -
2f
Wang ZY.Shi HX.Shi HJ. Synth. Commun. 2001, 31: 2841 -
3a
Amir M.Shikha K. Eur. J. Med. Chem. 2004, 39: 535 -
3b
Omar FA.Mahfouz NM.Rahman MA. Eur. J. Med. Chem. 1996, 31: 819 -
4a
Aboraia AS.Abdel-Rahman HM.Mahfouz NM.El-Gendy MA. Bioorg. Med. Chem. 2006, 14: 1236 -
4b
Rostom SAF.Shalaby MA.El-Demellawy MA. Eur. J. Med. Chem. 2003, 38: 959 -
4c
Abadi AH.Eissa AAH.Hassan GS. Chem. Pharm. Bull. 2003, 51: 838 -
5a
Mamolo MG.Zampieri D.Vio L.Fermeglia M. Bioorg. Med. Chem. 2005, 13: 3797 -
5b
Macaev F.Rusu G.Pogrebnoi S.Gudima A. Bioorg. Med. Chem. 2005, 13: 4842 -
5c
Khanum SA.Shashikanth S.Umesha S.Kavitha R. Eur. J. Med. Chem. 2005, 40: 1156 -
5d
Li Y.Liu J.Zhang HQ.Yang XP.Liu ZJ. Bioorg. Med. Chem. Lett. 2006, 16: 2278 - 6
Mekuskiene G.Tumkevicius S. J. Chem. Res., Synop. 2002, 213 - 7
Hassan AA.El-Shaieb KM.Shaker RM.Döpp D. Heteroat. Chem. 2005, 16: 12 -
8a
Berghot MA. Arch. Pharm. Res. 2001, 24: 263 -
8b
Golovlyova SM.Moskvichev YA.Alov EM. Chem. Heterocycl. Compd. (Engl. Transl.) 2001, 37: 1102 -
9a
Atta SMS.Fawzy NM.Ahmed FA. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 863 -
9b
Keshk EM.Abu-Hashem AA.Girges MM. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 1577 -
10a
Zou XJ.Lai LH.Jin GY.Zhang ZX. J. Agric. Food Chem. 2002, 50: 3757 -
10b
Wang XC.Li Z.Wei BG.Yang JY. Synth. Commun. 2002, 32: 1097 -
11a
Chen RY.Zhou J. Chin. Chem. Lett. 1996, 6: 539 -
11b
Chen RY.Zhou J. Heteroat. Chem. 1998, 9: 585 -
11c
Zhu XF.Li YG. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 128: 1 -
12a
Aucagne V.Amblard F.Agrofoglio LA. Synlett 2004, 2406 -
12b
Marshall JA.Liao J. J. Org. Chem. 1998, 63: 5962 -
12c
Marshall J.Wolf MA.Wallace EM. J. Org. Chem. 1997, 62: 367 -
13a
Budriesi R.Bisi A.Ioan P. Bioorg. Med. Chem. 2005, 13: 3423 -
13b
Yan Z.Kern ER.Gullen E. J. Med. Chem. 2005, 48: 91 -
13c
Meier C.Ducho C.Gorbig U. J. Med. Chem. 2004, 47: 2839 -
13d
Jiang Y.Han J.Yu C. J. Med. Chem. 2006, 49: 4333 -
14a
Sierecki E.Turcaud S.Martens T.Royer J. Synthesis 2006, 3199 -
14b
Cullis PM.Fawcett J.Griffith GA.Harger MJP.Lee M. J. Am. Chem. Soc. 2001, 123: 4147 -
14c
Zhou J.Chen RY. J. Chem. Soc., Perkin Trans. 1 1998, 2917 -
15a
Sulsky R.Robl JA.Biller SA. Bioorg. Med. Chem. Lett. 2004, 14: 5067 -
15b
Ma ZH.Shao RL.Ma HM.Cheng JR.Huang RQ. Chem. J. Chin. Univ. 1999, 20: 1574 - 16
Feng DX.Chen RY.Huang Y. Chem. J. Chin. Univ. 2006, 27: 2319 -
17a
Weener JW.Versleijen JPG. Eur. J. Org. Chem. 1998, 1511 -
17b
Westheimer FH. Acc. Chem. Res. 1968, 1: 70 - 18
Gorenstein DG. Prog. Nucl. Magn. Reson. Spectrosc. 1984, 16: 1