[3+2] Cycloadditions: Part XXXIV: Further Investigations of Cycloadditions of C,N-Diaryl- and C-Aryl-N-methyl Nitrones to &alpha;,&beta;-Unsaturated Esters

Sumana Sengupta; Avijit Banerji

doi:10.14233/ajchem.2019.22232

Issue

Vol. 31 No. 12 (2019): Vol 31 Issue 12

Issue Published : November 16, 2019

This work is licensed under a Creative Commons Attribution 4.0 International License.

[3+2] Cycloadditions: Part XXXIV: Further Investigations of Cycloadditions of C,N-Diaryl- and C-Aryl-N-methyl Nitrones to α,β-Unsaturated Esters

https://doi.org/10.14233/ajchem.2019.22232

Sumana Sengupta

Department of Chemistry, Chandernagore College, Chandernagore, Hooghly-712136, India & Centre of Advanced Studies on Natural Products including Synthesis, Department of Chemistry, University College of Science and Technology, University of Calcutta, Kolkata-700009, India

Avijit Banerji

Department of Chemistry, Chandernagore College, Chandernagore, Hooghly-712136, India & Central Ayurveda Research Institute for Drug Development, Kolkata-700091, India

Corresponding Author(s) : Sumana Sengupta

sngsumana@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 12 (2019): Vol 31 Issue 12
Article Published : November 16, 2019

Abstract

Investigations of [3+2] cycloadditions of C,N-diaryl and C-aryl-N-methyl nitrones as three atom components (TAC) to substituted methyl E-cinnamates and diethyl arylidene malonates have been further investigated. [3+2] Cycloadditions of cinnamates yielded mixtures of cycloadducts, the major products being the 3,4-trans-4,5-trans-2,3,5-triaryl-4-carbomethoxy products originating from the endo-carbonyl-exo-aryl meta channel approach of the cinnamate component. [3+2] Cycloadditions to diethyl arylidene malonates furnished single cycloadducts-3,5-trans-2-methyl-3,5-diaryl-4,4- dicarbethoxy isoxazolidines by a endo-aryl meta channel approach of the 2π-component.

Keywords

[3 2] Cycloadditions Methyl E-Cinnamate Diarylidene malonate Nitrone Isoxazolidine XRD

Sengupta, S., & Banerji, A. (2019). [3+2] Cycloadditions: Part XXXIV: Further Investigations of Cycloadditions of C,N-Diaryl- and C-Aryl-N-methyl Nitrones to α,β-Unsaturated Esters. Asian Journal of Chemistry, 31(12), 2777–2784. https://doi.org/10.14233/ajchem.2019.22232

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References

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References

A. Banerji, S. Sengupta, T. Prangé and A. Neuman, Indian J. Heterocycl. Chem., 28, 65 (2018).

S. Mandal, K.K. Maiti, A. Banerji, T. Prangé, A. Neuman and N. Acharjee, Indian J. Chem., 57B, 108 (2018).

A. Ghosh, A. Banerji and J. Banerji, J. Indian Chem. Soc., 91, 1393 (2014).

K.B.G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH: New York (1988);

H. Feuer, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, John Wiley & Sons: New York, edn 2 (2008).

A. Padwa, 1,3-Dipolar Cycloaddition Chemistry, Wiley InterScience, vols. 1 & 2 (1984);

A. Padwa and W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry towards Heterocycles and Natural Products, John Wiley & Sons, New York, Chap. 1 (2002).

A. Banerji and A. Sahu, J. Sci. Ind. Res., 45, 355 (1986).

A. Banerji and P. Sengupta, J. Indian Inst. Sci., 81, 313 (2001).

R. Huisgen, R. Grashey, H. Hauck and H. Seidl, Chem. Ber., 102, 736, (1969); https://doi.org/10.1002/cber.19691020305.

N. Acharjee, A. Banerji and B. Gayen, J. Indian Chem. Soc., 88, 1857 (2011).

A. Banerji, K.K. Maiti, S. Haldar, C. Mukhopadhyay, J. Banerji, T. Prangé and A. Neuman, Monatsh. Chem., 131, 901 (2000);https://doi.org/10.1007/s007060070068.

N. Acharjee, A. Banerji and T. Prangé, Monatsh. Chem., 141, 1213 (2010); https://doi.org/10.1007/s00706-010-0393-2.

A. Banerji, S. Dasgupta, P. Sengupta, T. Prangé and A. Neuman, Indian J. Chem., 43B, 1925 (2004).

N. Acharjee and A. Banerji, Comput. Theor. Chem., 967, 50 (2011); https://doi.org/10.1016/j.comptc.2011.03.040.

A. Banerji, P.K. Biswas, D. Bandyopadhyay, M. Gupta, T. Prangé and A. Neuman, J. Heterocycl. Chem., 44, 137 (2007); https://doi.org/10.1002/jhet.5570440122.

A. Banerji, D. Bandyopadhyay, P. Sengupta, B. Basak, T. Prangé and A. Neuman, Tetrahedron Lett., 47, 3827 (2006); https://doi.org/10.1016/j.tetlet.2006.03.168.

P.K. Biswas, D. Bandyopadhyay, T. Prangé, A. Neuman and A. Banerji, Synth. Commun., 41, 1146 (2011); https://doi.org/10.1080/00397911003797858.

A. Banerji, S. Sengupta, A. Nayak, P.K. Biswas, B. Bhattacharya, S. Dasgupta, R. Saha, T. Prangé and A. Neuman, Indian J. Chem., 46B, 9 (2007).

A. Ghosh, A. Banerji and J. Banerji, J. Indian Chem. Soc., 93, 359 (2016).

N. Acharjee, T.K. Das, A. Banerji, M. Banerjee and T. Prangé, J. Phys. Org. Chem., 23, 1187 (2010); https://doi.org/10.1002/poc.1690.

M. Jouçla, D. Grée and J. Hamelin, Tetrahedron, 29, 2315 (1973); https://doi.org/10.1016/S0040-4020(01)93355-1.

M. Jouçla and J. Hamelin, J. Chem. Res. (S), 276 (1978).

H. Gilman and A.H. Blatt, Organic Syntheses Collection, John Wiley & Sons: New York, vol. 1, p. 78 (1941).

E.C. Horning, Organic Syntheses Collection, John Wiley & Sons: New York, vol. 3, p. 372 (1955).

A.I. Vogel, A Text Book of Practical Organic Chemistry, Longmans: London, edn 4, p. 402 (1978).

G.M. Sheldrick and T.R. Schneider, Methods Enzymol., 277, 319 (1997);https://doi.org/10.1016/S0076-6879(97)77018-6.

A.L. Speck, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands (2001).