Synthesis of (5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one and Some N-Acyl Derivatives from (R)-Phenylglycine

Alessandro Rodrigues; Paulo Roberto Olivato; Roberto Rittner

doi:10.1055/s-2005-872101

PAPER

Synthesis of (5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one and Some N-Acyl Derivatives from (R)-Phenylglycine

Alessandro Rodrigues*^a, Paulo Roberto Olivato*^a, Roberto Rittner^b
^a Conformational Analysis and Electronic Interactions Laboratory, Instituto de Química, Universidade de São Paulo, C.P. 26077, São Paulo, SP 05513-970, Brazil
Fax: +55(11)38155579; e-Mail: alessand@iq.usp.br; e-Mail: prolivat@iq.usp.br;
^b Physical Organic Chemistry Laboratory, Chemistry Institute, State University of Campinas, C.P. 6154, Campinas, SP 13084-971, Brazil

Abstract

All articles of this category

Abstract

(5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one was synthesized from (R)-phenylglycine in five steps and in 65% overall yield. In addition, a convenient and practical method for N-acylation of 1,3,4-oxadiazinan-2-one directly with acids in the presence of DCC and catalytic quantities of DMAP is described. The acylated products were obtained in excellent yields.

Key words

(R)-phenylglycine - 1,3,4-oxadiazinan-2-ones - heterocycles - acylation - carboxylic acids

Full Text

References

1a Trepanier DL. Elbe JN. Harris GH. J. Med. Chem. 1968, 11: 357

1b Trepanier DL, and Harris GH. inventors; US Patent 3,377,345. ; Chem. Abstr. 1969, 70, 78026c

2a Casper DM. Burgeson JR. Esken JM. Ferrence GM. Hitchcock SR. Org. Lett. 2002, 4: 3739

2b Casper DM. Hitchcock SR. Tetrahedron: Asymmetry 2003, 14: 517

2c Hoover TR. Hitchcock SR. Tetrahedron: Asymmetry 2003, 14: 3233

2d Burgeson JR. Renner MK. Haradt I. Ferrence GM. Standard JM. Hitchcock SR. J. Org. Chem. 2004, 69: 727

3 Hitchcock SR. Nora GP. Casper DM. Squire MD. Maroules CD. Ferrence GM. Szczepura LF. Standard JM. Tetrahedron 2001, 57: 9789

4 Sheehan JC. Yang Ding-Djong H. J. Am. Chem. Soc. 1958, 80: 1154

5a Brown HC. Subba Rao BC. J. Am. Chem. Soc. 1960, 82: 681

5b McKennon MJ. Meyers AI. Drauz K. Schwarm M. J. Org. Chem. 1993, 58: 3568

6 Corey EJ. McCaully RJ. Sachdev HS. J. Am. Chem. Soc. 1970, 92: 2476

7 Takahashi H. Suzuki Y. Chem. Pharm. Bull. 1983, 31: 4295

8

This product was used without further purification, is quite sensitive, and had to be stored at -20 °C to avoid decomposition.

9 Nachman RJ. J. Heterocycl. Chem. 1982, 19: 1545

10 Hassner A. Alexanian V. Tetrahedron Lett. 1978, 4475

11 Höfle G. Steglich W. Vorbrüggen H. Angew. Chem., Int. Ed. Engl. 1978, 17: 569

12 Shiraiwa T. Miyazaki H. Imal T. Sunami M. Kurokawa H. Bull. Chem. Soc. Jpn. 1987, 60: 661