Solid phase-solid state synthesis of N-alkyl imides from anhydrides

Synlett

Volumn , Issue 10, 1999, Pages 1597-1599

  Chandrasekhar, S ^a   Padmaja, M B ^a   Raza, A ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Microwave; Solid phase; Solid state; Trifluoroacetic acid

Indexed keywords

ACID ANHYDRIDE; IMIDE; POLYMER; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL STRUCTURE; MICROWAVE RADIATION; PHASE TRANSITION; SOLID; SYNTHESIS;

EID: 0032848529     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2894     Document Type: Article

References (18)

1. (a) Toda, F. Acc. Chem. Res. 1995, 28, 480.
2. (b) Toda, F; Koji, K.; Yagi, M. Angew. Chem. Int. Ed. Engl. 1989, 28, 320
3. Loopy, A.; Petit, A.; Hamelin, J; Boulet, F. T.; Jacqualt, P.; Mathe, D. Synthesis 1998, 9, 1213
4. Encyclopedia Of Polymer Science and Engineering, Second Edn., Edited by Kroshwitz, J. I.; A Wiley-Interscience Publication. Kundela, V.7798.
5. Chandrasekhar, S.; Takhi, M.; Uma, G. Tetrahedron Lett. 1997,38,8089.
6. Chandrasekhar, S.; Reddy, B. V. S. Synlett 1998, 851.
7. Chandrasekhar, S.; Raza, A.; Padmaja, M. B. Synlett 1999, 1061.
8. The mesh filter is not very efficient in separation of silica gel (finer than 200 mesh) and resin (≈150μ) is used. However, by use of resin with more than 300μ (commercially available from polymer laboratories, USA) should enable easy separation. In the present instance Merrifield resin (150-300μ) is used.
9. Steele, J.; Gordon, D. W. Bio Med.Chem.Lett.1995, 5, 47.
10. Chandrasekhar, S.; Takhi, M.; Reddy, Y. R.; Mohapatra, S.; Rao, C. R.; Reddy, K. V. Tetrahedron 1997, 53, 14997.
11. Refluxed in benzene for 8h followed by standard workup and cleavage afforded the corresponding acids in less than 30% yield.
12. a) Pai, L. A.; Pastan, I.; Ram B. P.; JAMA, 1993, 269, 78.,
13. b) Tyle, P. Pharm, Res. 1987, 4, 181;
14. c) Pretesz, G. A.; Mckenzie, I. F. C. Immun. Rev., 1992, 57;
15. d) Rich, D. H.; Gellchen, P. D.; Tong, A.; Buckner, C. K. J.Med.Chem., 1964, 18;
16. e) Baldwin, S. W.; Greenspan, P.; Alaimo, C.; McPhail, A. T. Tetrahedron Lett. 1991, 32, 5877.;
17. f) Arai, Y.; Matsui, M.;A.; Kontani, T.; Ohno, T.;K Oizumi, T.; Shiro, M.;J.Chem.Soc., Perkin Trans.1 1994,25.
18. BPL SANYO (600 watts) domestic microwave was used with an output at 75% for 5 minutes (after each minute, the reaction mixture is thoroughly agitated).