Synthesis of Some Novel Class of Bis(isoxazoline) and Bis(aziridine) Derivatives
Corresponding Author
Bhaskar Chakraborty
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
E-mail: [email protected]Search for more papers by this authorManjit Singh Chettri
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
Search for more papers by this authorGovinda Prasad Luitel
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
Search for more papers by this authorCorresponding Author
Bhaskar Chakraborty
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
E-mail: [email protected]Search for more papers by this authorManjit Singh Chettri
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
Search for more papers by this authorGovinda Prasad Luitel
Organic Chemistry Laboratory, Sikkim Government College, Gangtok, Sikkim, 737 102 India
Search for more papers by this authorAbstract
Synthesis of some new bis(isoxazoline) derivatives has been described from terepthaldehyde derived bis(nitrones) using microwave irradiation via 1,3-dipolar cycloaddition reaction. Bis(isoxazoline) derivatives in turn successfully converted into new bis(aziridine) derivatives via Baldwin rearrangement. Simple reaction methodology, non involvement of catalysts, and good to excellent yields are the important features noticed in this synthesis.
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References and Notes
- 1Padwa, A.; Pearson, W. H. Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Wiley: New Jersey, 2003.
10.1002/0471221902 Google Scholar
- 2Kobayashi, S.; Jørgensen, K. A. Cycloaddition Reactions in Organic Synthesis; Wiley-VCH: Weimheim, 2002.
- 3Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew Chem Int Edn 2005, 44, 3275.
- 4Cinar, H.; Tabatabai, M.; Ritter, H. Polym Int 2012, 61, 692.
- 5Raspertova, I.; Osetska, O.; Gubina, K.; Lampeka, R. Polyhedron 2011, 30, 2320.
- 6Oh, Y. S.; Kotani, S.; Sugiura, M.; Nakajima, M. Tetrahedron: Asymmetry 2010, 21, 1833.
- 7Chakraborty, B.; Luitel, G. P. J Heterocyclic Chem 2015, 52, 1260.
- 8Miyamoto, Y.; Wada, N.; Soeta, T.; Fujinami, S.; Inomata, K.; Ukaji, U. Chem Asian J 2013, 8, 824.
- 9Ishikawa, T.; Kudoh, T.; Yoshida, J.; Yasuhara, A.; Manabe, S.; Saito, S. Org Lett 2002, 4, 1907.
- 10Tanaka, K.; Ohsuga, M.; Sugimato, Y.; Okafuji, Y.; Mitsuhashi, K. J Fluorine Chem 1988, 39, 39.
- 11Degennaro, L.; Trinchera, P.; Luisi, R. Chem Rev 2014, 114, 7881.
- 12Padwa, A. In Comprehensive Heterocyclic Chemistry III; A. R. Katrizky; C. A. Ramsden; E. F. V. Scriven; R. J. K. Taylor, Eds.; Elsevier: New York, 2008; Vol 1, pp 1–104.
10.1002/9780470187371.ch1 Google Scholar
- 13Sweeney, J. B. In Science of Synthesis; E. Schaumann; D. Enders, Eds.; George Thieme Verlag: Stuttgart, Germany, 2008; Vol 40a, pp 643.
- 14 A. K. Yudin (Ed) Aziridines and Epoxides in Organic Synthesis; Wiley-VCH: Weinheim, 2006.
10.1002/3527607862 Google Scholar
- 15Zwanenburg, B.; ten Holte, P. Top Curr Chem 2001, 216, 93.
- 16Baldwin, J. E.; Pudussery, R. G.; Qureshi, A. K.; Sklarz, B. J Am Chem Soc 1968, 90, 5325.
- 17Freeman, J. P. Chem Rev 1983, 83, 241.
- 18Pinho e Melo, T. M. V. D. Eur J Org Chem 2010, 18, 3363.
- 19Chakraborty, B.; Luitel, G. P. Tetrahedron Lett 2013, 54, 765.
- 20Chakraborty, B.; Sharma, P. K.; Kafley, S. Green Chem Lett Rev 2013, 6, 141.
- 21Chakraborty, B.; Sharma, P. K.; Chhetri, M. S. J Heterocyclic Chem 2012, 49, 1260.
- 22Chakraborty, B.; Sharma, P. K. Synth Commun 2012, 42, 1804.
- 23Tanner, D. Angew Chem Int Ed Engl 1994, 33, 599.
- 24Padwa, A. In Comprehensive Heterocyclic Chemistry-Vol III; A. R. Katritzky, Ed.; Elsevier: Oxford, 2008; Vol 18, pp 1–97.
10.1002/9780470187388.ch1 Google Scholar
- 25Sweeney, J. B. In Science of Synthesis; E. Shaumann; D. Enders, Eds.; Thieme: Stuttgart, 2009; Vol 40a Chapter 40.1.5.
- 26Schneider, C. Angew Chem Int Ed Engl 2009, 48, 2082.
- 27Dauban, P.; Malik, G. Angew Chem Int Ed Engl 2009, 48, 9026.
- 28Lu, P. Tetrahedron 2010, 66, 2549.
- 29Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry: A. Padwa, Ed.; Wiley-Interscience: NY, 1984; Vol 2 Chapter 9, pp 83–168.
- 30Confalone, P. N.; Huie, E. M. Org React 1988, 36, 1.
- 31Etiemey, J. P.; Lidstrom, P. Microwave Assisted Organic Synthesis; Blackwell Publishing: Oxford, 2005.
- 32Loupy, A. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
10.1002/3527601775 Google Scholar
- 33Marquez, H.; Loupy, A.; Calderon, O.; Perez, E. Tetrahedron 2006, 62, 2616.
- 34Deshong, P.; Li, W.; Kennington, J. W. Jr.; Ammon, H. L.; Leginus, J. M. J Org Chem 1991, 56, 1364.
