Microwave assisted rupture of furoxans to nitrile oxides and intermolecular capture by dipolarophiles

Synthetic Communications

Volumn 28, Issue 13, 1998, Pages 2415-2420

  Karmakar, Dipankar ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIARYLFUROXAN DERIVATIVE; 3,4 DIBENZOYLFUROXAN DERIVATIVE; FUROXAN; ISOXAZOLE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; MICROWAVE IRRADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0031752168     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004293     Document Type: Article

References (19)

1. Werner, A.; and Buss, A., Chem. Ber., 1894, 27, 2193; Torssell, K. B. G., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH Publishers. Inc. New York 1988, p 66.
2. Werner, A.; and Buss, A., Chem. Ber., 1894, 27, 2193; Torssell, K. B. G., Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH Publishers. Inc. New York 1988, p 66.
3. Ackrell, J.; Altaf-ur-ahman, M.; Boulton, A. J.; and Brown, R. C., J. Chem. Soc. Perkin Trans 1, 1972, 1587; Dondoni, A.; Barbaro, G.; Battaglia, A.; and Giorgianni, P., J. Org. Chem., 1972, 37, 3196.
4. Ackrell, J.; Altaf-ur-ahman, M.; Boulton, A. J.; and Brown, R. C., J. Chem. Soc. Perkin Trans 1, 1972, 1587; Dondoni, A.; Barbaro, G.; Battaglia, A.; and Giorgianni, P., J. Org. Chem., 1972, 37, 3196.
5. Grundmann, C.; and Grunanger, P., The Nitrile Oxide, Springer-Verlag West Berlin, Heidelberg, New York, 1971, p 56, 79, 215 and references cited therein. For the cycloreversion of furoxans see: Gabriel, S.; and Koppe, M., Chem. Ber., 1886, 19, 1145; Shimizu, T.; Hayashi, Y.; Taniguchi, T.; and Teramura, K., Tetrahedron, 1985, 41, 727; Shimizu, T.; Hayashi, Y.; and Teramura, K., J. Org. Chem., 1983, 48, 3053.
6. Grundmann, C.; and Grunanger, P., The Nitrile Oxide, Springer-Verlag West Berlin, Heidelberg, New York, 1971, p 56, 79, 215 and references cited therein. For the cycloreversion of furoxans see: Gabriel, S.; and Koppe, M., Chem. Ber., 1886, 19, 1145; Shimizu, T.; Hayashi, Y.; Taniguchi, T.; and Teramura, K., Tetrahedron, 1985, 41, 727; Shimizu, T.; Hayashi, Y.; and Teramura, K., J. Org. Chem., 1983, 48, 3053.
7. Grundmann, C.; and Grunanger, P., The Nitrile Oxide, Springer-Verlag West Berlin, Heidelberg, New York, 1971, p 56, 79, 215 and references cited therein. For the cycloreversion of furoxans see: Gabriel, S.; and Koppe, M., Chem. Ber., 1886, 19, 1145; Shimizu, T.; Hayashi, Y.; Taniguchi, T.; and Teramura, K., Tetrahedron, 1985, 41, 727; Shimizu, T.; Hayashi, Y.; and Teramura, K., J. Org. Chem., 1983, 48, 3053.
8. Grundmann, C.; and Grunanger, P., The Nitrile Oxide, Springer-Verlag West Berlin, Heidelberg, New York, 1971, p 56, 79, 215 and references cited therein. For the cycloreversion of furoxans see: Gabriel, S.; and Koppe, M., Chem. Ber., 1886, 19, 1145; Shimizu, T.; Hayashi, Y.; Taniguchi, T.; and Teramura, K., Tetrahedron, 1985, 41, 727; Shimizu, T.; Hayashi, Y.; and Teramura, K., J. Org. Chem., 1983, 48, 3053.
9. Chapman, J. A.; Crosby, J.; Cummings, C. A.; Rennic, R. A. C.; and Paton, R. M., J. Chem. Soc. Chem. Commun., 1976, 240; For the pyrolysis of furoxans see: Mitchell, W. R.; and Paton, R. M., Tetrahedron Lett., 1979, 2443; Whitney, R. A.; and Nicholas, E. S., Tetrahedron Lett., 1981, 3371
10. Chapman, J. A.; Crosby, J.; Cummings, C. A.; Rennic, R. A. C.; and Paton, R. M., J. Chem. Soc. Chem. Commun., 1976, 240; For the pyrolysis of furoxans see: Mitchell, W. R.; and Paton, R. M., Tetrahedron Lett., 1979, 2443; Whitney, R. A.; and Nicholas, E. S., Tetrahedron Lett., 1981, 3371
11. Chapman, J. A.; Crosby, J.; Cummings, C. A.; Rennic, R. A. C.; and Paton, R. M., J. Chem. Soc. Chem. Commun., 1976, 240; For the pyrolysis of furoxans see: Mitchell, W. R.; and Paton, R. M., Tetrahedron Lett., 1979, 2443; Whitney, R. A.; and Nicholas, E. S., Tetrahedron Lett., 1981, 3371
12. Otsuji, Y.; Tsujii, Y.; Yoshida, A.; and Imoto, E., Bull. Chem. Soc. Jpn., 1971, 44, 223.
13. Brittelli, D. R.; and Boswell, G. A. Jr., J. Org. Chem., 1981, 46, 316.
14. Altaf-ur-Rahman, M.; Boulton, A. J.; and Middleton, D., Tetrahedron Lett., 1972, 3469.
15. The application of microwave energy to effect a variety of chemical process has blossomed rapidly in the past few years. From its use in moisture analysis it has been applied to a number of organic reactions. For some recent reviews see: Caddick, S.; Tetrahedron 1995, 51, 10403; Mingos, D. M.; and Baghurs, D. R., Chem. Soc. Rev., 1991, 20, 1-4; Biguere, R. J.; in Organic Synthesis Theory and Application, JAI Press 1989, 1, 103-172; Bose, A. K.; Manhas, M. S.; Ghosh, M. M.; Raju, V. S.; Bari, S. S.; Bewaz, S. N.; Banik, B. K.; Choudhury, A. G.; and Borakat, K. J., J. Org. Chem., 1991, 56, 6968; For the superheating and acceleration effects see: Bughurst, D. R.; and Mingos, D. M. P., J. Chem. Soc. Chem. Commun., 1992, 674.
16. The application of microwave energy to effect a variety of chemical process has blossomed rapidly in the past few years. From its use in moisture analysis it has been applied to a number of organic reactions. For some recent reviews see: Caddick, S.; Tetrahedron 1995, 51, 10403; Mingos, D. M.; and Baghurs, D. R., Chem. Soc. Rev., 1991, 20, 1-4; Biguere, R. J.; in Organic Synthesis Theory and Application, JAI Press 1989, 1, 103-172; Bose, A. K.; Manhas, M. S.; Ghosh, M. M.; Raju, V. S.; Bari, S. S.; Bewaz, S. N.; Banik, B. K.; Choudhury, A. G.; and Borakat, K. J., J. Org. Chem., 1991, 56, 6968; For the superheating and acceleration effects see: Bughurst, D. R.; and Mingos, D. M. P., J. Chem. Soc. Chem. Commun., 1992, 674.
17. The application of microwave energy to effect a variety of chemical process has blossomed rapidly in the past few years. From its use in moisture analysis it has been applied to a number of organic reactions. For some recent reviews see: Caddick, S.; Tetrahedron 1995, 51, 10403; Mingos, D. M.; and Baghurs, D. R., Chem. Soc. Rev., 1991, 20, 1-4; Biguere, R. J.; in Organic Synthesis Theory and Application, JAI Press 1989, 1, 103-172; Bose, A. K.; Manhas, M. S.; Ghosh, M. M.; Raju, V. S.; Bari, S. S.; Bewaz, S. N.; Banik, B. K.; Choudhury, A. G.; and Borakat, K. J., J. Org. Chem., 1991, 56, 6968; For the superheating and acceleration effects see: Bughurst, D. R.; and Mingos, D. M. P., J. Chem. Soc. Chem. Commun., 1992, 674.
18. The application of microwave energy to effect a variety of chemical process has blossomed rapidly in the past few years. From its use in moisture analysis it has been applied to a number of organic reactions. For some recent reviews see: Caddick, S.; Tetrahedron 1995, 51, 10403; Mingos, D. M.; and Baghurs, D. R., Chem. Soc. Rev., 1991, 20, 1-4; Biguere, R. J.; in Organic Synthesis Theory and Application, JAI Press 1989, 1, 103-172; Bose, A. K.; Manhas, M. S.; Ghosh, M. M.; Raju, V. S.; Bari, S. S.; Bewaz, S. N.; Banik, B. K.; Choudhury, A. G.; and Borakat, K. J., J. Org. Chem., 1991, 56, 6968; For the superheating and acceleration effects see: Bughurst, D. R.; and Mingos, D. M. P., J. Chem. Soc. Chem. Commun., 1992, 674.
19. The application of microwave energy to effect a variety of chemical process has blossomed rapidly in the past few years. From its use in moisture analysis it has been applied to a number of organic reactions. For some recent reviews see: Caddick, S.; Tetrahedron 1995, 51, 10403; Mingos, D. M.; and Baghurs, D. R., Chem. Soc. Rev., 1991, 20, 1-4; Biguere, R. J.; in Organic Synthesis Theory and Application, JAI Press 1989, 1, 103-172; Bose, A. K.; Manhas, M. S.; Ghosh, M. M.; Raju, V. S.; Bari, S. S.; Bewaz, S. N.; Banik, B. K.; Choudhury, A. G.; and Borakat, K. J., J. Org. Chem., 1991, 56, 6968; For the superheating and acceleration effects see: Bughurst, D. R.; and Mingos, D. M. P., J. Chem. Soc. Chem. Commun., 1992, 674.