Facile One-Pot Method for the Synthesis of Novel N-Dichloroacetyl-1,3-oxazolidines

REFERENCES

• Agami , C. ; Couty , F. The use of N-boc-1,3-oxazolidines as chiral auxiliaries in asymmetric synthesis . Eur. J. Org. Chem. 2004 , 4 , 677 – 685 .
   Google Scholar
• Iwata , A. ; Tang , H. ; Kunai , A. ; Ohshita , J. ; Yamamoto , Y. ; Matui , C. Ring-opening reactions of cyclic acetals and 1,3-oxazolidines with halosilane equivalents . J. Org. Chem. 2002 , 67 ( 15 ), 5170 – 5175 .
   Google Scholar
• Agami , C. ; Comesse , S. ; Kadouri-Puchot , C. Asymmetric syntheses of new functionalized β-amino alcohols via diastereoselective addition of organometallic reagents onto oxazolidines . J. Org. Chem. 2002 , 67 ( 5 ), 1496 – 1500 .
   Google Scholar
• Adam , W. ; Schambony , S. B. Diastereoselective epoxidation of oxazolidine-substituted alkenes by dimethyldioxirane and m-chloroperbenzoic acid: Facial control through hydrogen bonding by the urea functionality . Org. Lett. 2001 , 3 ( 1 ), 79 – 82 .
   Google Scholar
• Blanchet , J. ; Micouin , B. L. ; Husson , H.-P. Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines . J. Org. Chem. 2000 , 65 , 6423 – 6426 .
   Google Scholar
• Matola , T. ; Jablonkai , I. Safening efficacy of halogenated acetals, ketals, and amides and relationship between the structure and effect on glutathione and glutathione S-transferases in maize . Crop Protection. 2007 , 26 ( 3 ), 278 – 284 .
   Google Scholar
• Katarzyna , B. ; Dorota , S. ; Tadeusz , G. A concise synthesis of protected diethyl 1-amino-2-hydroxyalkylphosphonates . Tetrahedron Lett. 2003 , 44 ( 25 ), 4747 – 4750 .
   Google Scholar
• Guirado , A. ; Andreu , R. ; Galvez , J. Direct conversion of 4-amino-2-phenyl-2-oxazolines into either 2-arylimino-1,3-oxazolidine or 2-arylimino-1,3-thiazolidine hydrochlorides . Tetrahedron Lett. 2003 , 44 ( 19 ), 3809 – 3821 .
   Google Scholar
• Kirsten , S. ; Frank , G. Efficient oxidative synthesis of 2-oxazolines . Synthesis 2006 , 18 , 2996 – 3002 .
   Google Scholar
• Katritzky , A. R. ; Feng , D. ; Qi , M. The synthesis of 3,5-di- and 3,5,5-trisubstituted-1,3-oxazolidines from primary amines and carbonyl compounds . Tetrahedron Lett. 1998 , 39 ( 38 ), 6835 – 6836 .
   Google Scholar
• Taylor , W. G. ; Schreck , C. E. Synthesis and mosquito repellent properties of some 2-alkyl-N-acetyloxazolidines . Pestic. Sci. 1991 , 33 ( 1 ), 1 – 9 .
   Google Scholar
• Wesley , G. T. ; Tse , W. H. ; Carl , E. S. Synthesis and mosquito repellent properties of 2,2-dialkyl- and -2-alkyl-4,4-dimethyl-N-acetyloxazolidines . Pestic. Sci. 1996 , 46 ( 4 ), 307 – 314 .
   Google Scholar
• Jiying , C. ; Qinfen , H. ; Wensheng , C. ; Fengze , L. Preparation of 2-hydroxyethylamine and 2-hydroxypropylmine . Pharm. Ind. 1987 , 18 ( 11 ), 14 – 16 .
   Google Scholar
• Nandkishor , N. K. ; Girdharilal , B. T. ; Sumit , V. G. Efficient oxidative conversion of aldehydes to 2-substituted oxazolines and oxazines using (diacetoxyiodo)benzene. Synlett 2007, 12, 1921–1924.
   Google Scholar
• Manas , K. G. ; Koena , G. Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds: Further support towards an SN2-type mechanism . Tetrahedron Lett. 2007 , 48 ( 18 ), 3191 – 3195 .
   Google Scholar