An expeditious synthesis of optically pure 1,4,5,6-tetrahydro-as-triazines, fused to the carbohydrate skeleton

作者: Muhammad Saeed , Raid J. Abdel-Jalil , Wolfgang Voelter , Mustafa M. El-Abadelah

DOI: 10.1246/CL.2001.660

关键词:

摘要: An easy and high yield one pot reaction to enantiomerically pure 1,4,5,6-tetrahydro-as-triazines 5a–d 8a–d is described, starting from benzyl 4-amino-2,3-anhydro-4-deoxy-β-L-lyxopyranoside (3) 4-amino-2,3-anhydro-4-deoxy-α-D-lyxopyranoside (6).

参考文章(6)
Raid J. Abdel-Jalil, Raed A. Al-Qawasmeh, Yousef Al-Abed, Wolfgang Voelter, A stereospecific synthesis of tetra-substituted chiral piperazines Tetrahedron Letters. ,vol. 39, pp. 7703- 7704 ,(1998) , 10.1016/S0040-4039(98)01677-3
Raid J Abdel-Jalil, Muhammad Saeed, Wolfgang Voelter, An expeditious approach to tri-substituted chiral thiazolines Tetrahedron Letters. ,vol. 42, pp. 2435- 2437 ,(2001) , 10.1016/S0040-4039(01)00188-5
Robert J. Ferrier, Sydney. Middleton, THE CONVERSION OF CARBOHYDRATE DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES Chemical Reviews. ,vol. 93, pp. 2779- 2831 ,(1993) , 10.1021/CR00024A008
Raed A. Al-Qawasmeh, Taleb H. Al-Tel, Raid J. Abdel-Jalil, Wolfgang Voelter, Carbohydrates to Heterocycles:A New Strategy for the Synthesis of Enantiomerically Pure Pyridazines and Oxazines Derived from Epoxypyranoside Scaffolds Chemistry Letters. ,vol. 1999, pp. 541- 542 ,(1999) , 10.1246/CL.1999.541
Donald L. Trepanier, Eugene R. Wagner, Guy Harris, Allan D. Rudzik, 1,4,5,6-Tetrahydro-as-triazines. I. Sulfuric Acid Catalyzed Condensation of Nitriles and Hydrazino Alcohols1 Journal of Medicinal Chemistry. ,vol. 9, pp. 881- 885 ,(1966) , 10.1021/JM00324A024
Mustafa M. El-Abadelah, Mustafa M. El-Abadelah, Ahmad Q. Hussein, Bassam A. Thaher, Heterocycles from Nitrile Imines. Part IV. Chiral 4,5-Dihydro-1,2,4-triazin-6-ones Heterocycles. ,vol. 32, pp. 1879- 1895 ,(1991) , 10.3987/COM-90-5637