Cycloaddition Reactions of Azatrienes with Sulfene
Affiliation(s)
Department of Chemistry, Durban University of Technology, Steve Biko Campus, Durban, South Africa.
Department of Chemistry, Durban University of Technology, Steve Biko Campus, Durban, South Africa.
ABSTRACT
Unprecedented cycloaddition reactions of azatrienes (1) with sulfene leading to the synthesis of functionalized thiazinedioxide derivatives (5) are described. The reactions were found be highly regioselective resulting in the formation of only [4 + 2] cycloadducts.
Unprecedented cycloaddition reactions of azatrienes (1) with sulfene leading to the synthesis of functionalized thiazinedioxide derivatives (5) are described. The reactions were found be highly regioselective resulting in the formation of only [4 + 2] cycloadducts.
Cite this paper
P. Singh and K. Bisetty, "Cycloaddition Reactions of Azatrienes with Sulfene," International Journal of Organic Chemistry, Vol. 2 No. 2, 2012, pp. 121-125. doi: 10.4236/ijoc.2012.22019.
P. Singh and K. Bisetty, "Cycloaddition Reactions of Azatrienes with Sulfene," International Journal of Organic Chemistry, Vol. 2 No. 2, 2012, pp. 121-125. doi: 10.4236/ijoc.2012.22019.
References
[1] B. Groenendaal, E. Ruijter and R. V. A. Orru, “1-Azadienes in Cycloaddition and Multicomponent Reactions to- wards N-heterocycles,” Journal of Chemical Society, Chemical Communications, No. 43, 2008, pp. 5474-5489. doi:10.1039/b809206k [2] M. Behforouz and M. Ahmadian, “Diels-Alder Reactions of 1-Azadienes,” Tetrahedron, Vol. 56, No. 30, 2000, pp. 5259-5288. doi:10.1016/S0040-4020(00)00259-3 [3] S. Jayakumar, M. P. S. Ishar and M. P. Mahajan, “Recent Advances in Synthetic Applications of Azadienes” Tet- rahedron, Vol. 58, No. 3, 2002, pp. 379-471. doi:10.1016/S0040-4020(01)01050-X [4] T. N. Danks and D. Velo-Rego, “Reaction of a Chromium Carbene Complex with 1-Azadienes and Synthesis of Trisubstituted Pyrroles,” Tetrahedron Letters, Vol. 35, No. 50, 1994, pp. 9443-9444. doi:10.1016/S0040-4039(00)78565-0 [5] J. Barluenga, M. Tomas, J. A. Lopez-Pelegrin and E. Rubio, “Stereselective Cyclopropanation of 1-Azadienes with Fischer Carbine Complexes,” Journal of Chemical Society, Chemical Communications, No. 6, 1995, pp. 665- 666. doi:10.1039/c39950000665 [6] Y. N. Romaschin, M. T. H. Liu and R. J. Bonneau, “The Facile Synthesis of 1,2,3-Trisubstituted Pyrroles from the Reaction of Chlorocarbenes with 1-Azabuta-1,3-dienes,” Journal of Chemical Society, Chemical Communications, No. 5, 1999, pp. 447-448. doi:10.1039/a809508f [7] M. Chagr, H. Fillion and A. Pougny, “A Regioselective Synthesis of 4,5- and 4,8-Disubstitutedazaanthraquinones by the Diels-Alder Route,” Tetrahedron Letters, Vol. 29, No. 46, 1988, pp. 5913-5916. doi:10.1016/S0040-4039(00)82224-8 [8] D. Berger and W. Imhof, “One-Pot Synthesis of γ-Lactams in a Reaction Cascade from α,β-Unsaturated Imines, CO and Ethylene Catalysed by Ru3(CO)12,” Journal of Chemical Society, Chemical Communications, No. 16, 1999, pp. 1457-1458. doi:10.1039/a903266e [9] J. Barluenga, I. Merino and S. Palacios, “One Pot Synthesis of 2-Vinyl-1-azadienes and Divinylketones,” Tetrahe- dron Letters, Vol. 30, No. 40, 1989, pp. 5493-5496. doi:10.1016/S0040-4039(01)80602-X [10] N. Martin, A. M. Grau, L. Sanchez, C. Seoane and M. Torres, “The First Hetero-Diels-Alder Reaction of 60?C with 1-Azadienes. Synthesis of Tetrahydropyrido [2’,3’: 1,2][60]fullerene Derivatives,” Journal of Organic Chemistry, Vol. 63, No. 22, 1998, pp. 8074-8076. [11] C. R. Berry and R. P. Hsung, “In-verse Electron-Demand Aza-[4 + 2] Cycloaddition Reactions of Allenamides,” Tet- rahedron, Vol. 60, No. 35, 2004, pp. 7629-7636. doi:10.1016/j.tet.2004.05.117 [12] R. C. Clark, S. Pfeiffer and D. L. Boger, “Diastereoselective Diels-Alder Reactions of N-Sulfonyl- 1-aza-1,3-butadienes with Optically Active Enol Ethers: An Asym-metric Variant of the 1-Azadiene Diels-Alder Reaction,” Journal of American Chemical Society, Vol. 128, No, 8, 2006, pp. 2587-2593. doi:10.1021/ja0571646 [13] M. He, R. Struble and J. W. Bode, “Highly Enantioselective Azadiene Diels-Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes,” Journal of American Chemical Society, Vol. 128, No. 26, 2006, pp. 8418-8420. doi:10.1021/ja062707c [14] A. Robin, K. Julienne, J. C. Meslin and D. Deniaud, “Syn- thesis of Pyridone and Pyridine Rings by [4 + 2] Hetero-Cyclocondensation,” Tetrahedron Letters, Vol. 45, No. 52, 2004, pp. 9557-9559. doi:10.1016/j.tetlet.2004.10.142 [15] M. C. Elliott, E. Kruiswijk and D. J. Willock, “Asymmetric Hetero-Diels-Alder Reactions. Reactions of Oxazolo [3,2-c]pyrimidines,” Tetrahedron, Vol. 57, No. 51, 2001, pp. 10139-10146. doi:10.1016/S0040-4020(01)01032-8 [16] D. L. Boger, “Diels-Alder Reactions of Azdienes,” Tet- rahedron, Vol. 39, No. 18, 1983, pp. 2869-2939. doi:10.1016/S0040-4020(01)92154-4 [17] D. L. Boger and S. M. Weinreb, “In Hetero Diels-Alder Methodology in Organic Synthesis,” Academic Press Inc., San Diego, 1987, p 239. [18] S. N. Mazumdar, M. Sharma and M. P. Mahajan, “Diels- Alder Cycloaddition Reactions of 1,3-Diazabutadienes with Sulfene,” Tetrahedron Letters, Vol. 28, No. 23, 1987, pp. 2641-2642. doi:10.1016/S0040-4039(00)96169-0 [19] P. Singh, G. Bhargava and M. P. Mahajan, “Tandem [2 + 2] Cycloaddition and Cope Rearrangement in Reactions of Cross-Conjugated Azatrienes with Conjugated Ketenes: A Facile Single Step Synthesis of Novel Azocinone Derivatives,” Tetrahedron, Vol. 62, No. 48, 2006, pp. 11267- 11273. doi:10.1016/j.tet.2006.09.007 [20] M. H. Elnagdi, S. M. Mousawi, M. M. Abdel-Khalik, S. El-Sheriny and E. John, “Studies with Enaminones: Reactivity of 1,5-Disubstituted-1,4-pentadien-3-ones toward Electrophilic Reagents. A Novel Route to Azolylazines, Benzofuranals, Pyranones,” Journal of Heterocyclic Chemistry, Vol. 38, No. 4, 2001, pp. 949-953. doi:10.1002/jhet.5570380422
[1] B. Groenendaal, E. Ruijter and R. V. A. Orru, “1-Azadienes in Cycloaddition and Multicomponent Reactions to- wards N-heterocycles,” Journal of Chemical Society, Chemical Communications, No. 43, 2008, pp. 5474-5489. doi:10.1039/b809206k [2] M. Behforouz and M. Ahmadian, “Diels-Alder Reactions of 1-Azadienes,” Tetrahedron, Vol. 56, No. 30, 2000, pp. 5259-5288. doi:10.1016/S0040-4020(00)00259-3 [3] S. Jayakumar, M. P. S. Ishar and M. P. Mahajan, “Recent Advances in Synthetic Applications of Azadienes” Tet- rahedron, Vol. 58, No. 3, 2002, pp. 379-471. doi:10.1016/S0040-4020(01)01050-X [4] T. N. Danks and D. Velo-Rego, “Reaction of a Chromium Carbene Complex with 1-Azadienes and Synthesis of Trisubstituted Pyrroles,” Tetrahedron Letters, Vol. 35, No. 50, 1994, pp. 9443-9444. doi:10.1016/S0040-4039(00)78565-0 [5] J. Barluenga, M. Tomas, J. A. Lopez-Pelegrin and E. Rubio, “Stereselective Cyclopropanation of 1-Azadienes with Fischer Carbine Complexes,” Journal of Chemical Society, Chemical Communications, No. 6, 1995, pp. 665- 666. doi:10.1039/c39950000665 [6] Y. N. Romaschin, M. T. H. Liu and R. J. Bonneau, “The Facile Synthesis of 1,2,3-Trisubstituted Pyrroles from the Reaction of Chlorocarbenes with 1-Azabuta-1,3-dienes,” Journal of Chemical Society, Chemical Communications, No. 5, 1999, pp. 447-448. doi:10.1039/a809508f [7] M. Chagr, H. Fillion and A. Pougny, “A Regioselective Synthesis of 4,5- and 4,8-Disubstitutedazaanthraquinones by the Diels-Alder Route,” Tetrahedron Letters, Vol. 29, No. 46, 1988, pp. 5913-5916. doi:10.1016/S0040-4039(00)82224-8 [8] D. Berger and W. Imhof, “One-Pot Synthesis of γ-Lactams in a Reaction Cascade from α,β-Unsaturated Imines, CO and Ethylene Catalysed by Ru3(CO)12,” Journal of Chemical Society, Chemical Communications, No. 16, 1999, pp. 1457-1458. doi:10.1039/a903266e [9] J. Barluenga, I. Merino and S. Palacios, “One Pot Synthesis of 2-Vinyl-1-azadienes and Divinylketones,” Tetrahe- dron Letters, Vol. 30, No. 40, 1989, pp. 5493-5496. doi:10.1016/S0040-4039(01)80602-X [10] N. Martin, A. M. Grau, L. Sanchez, C. Seoane and M. Torres, “The First Hetero-Diels-Alder Reaction of 60?C with 1-Azadienes. Synthesis of Tetrahydropyrido [2’,3’: 1,2][60]fullerene Derivatives,” Journal of Organic Chemistry, Vol. 63, No. 22, 1998, pp. 8074-8076. [11] C. R. Berry and R. P. Hsung, “In-verse Electron-Demand Aza-[4 + 2] Cycloaddition Reactions of Allenamides,” Tet- rahedron, Vol. 60, No. 35, 2004, pp. 7629-7636. doi:10.1016/j.tet.2004.05.117 [12] R. C. Clark, S. Pfeiffer and D. L. Boger, “Diastereoselective Diels-Alder Reactions of N-Sulfonyl- 1-aza-1,3-butadienes with Optically Active Enol Ethers: An Asym-metric Variant of the 1-Azadiene Diels-Alder Reaction,” Journal of American Chemical Society, Vol. 128, No, 8, 2006, pp. 2587-2593. doi:10.1021/ja0571646 [13] M. He, R. Struble and J. W. Bode, “Highly Enantioselective Azadiene Diels-Alder Reactions Catalyzed by Chiral N-Heterocyclic Carbenes,” Journal of American Chemical Society, Vol. 128, No. 26, 2006, pp. 8418-8420. doi:10.1021/ja062707c [14] A. Robin, K. Julienne, J. C. Meslin and D. Deniaud, “Syn- thesis of Pyridone and Pyridine Rings by [4 + 2] Hetero-Cyclocondensation,” Tetrahedron Letters, Vol. 45, No. 52, 2004, pp. 9557-9559. doi:10.1016/j.tetlet.2004.10.142 [15] M. C. Elliott, E. Kruiswijk and D. J. Willock, “Asymmetric Hetero-Diels-Alder Reactions. Reactions of Oxazolo [3,2-c]pyrimidines,” Tetrahedron, Vol. 57, No. 51, 2001, pp. 10139-10146. doi:10.1016/S0040-4020(01)01032-8 [16] D. L. Boger, “Diels-Alder Reactions of Azdienes,” Tet- rahedron, Vol. 39, No. 18, 1983, pp. 2869-2939. doi:10.1016/S0040-4020(01)92154-4 [17] D. L. Boger and S. M. Weinreb, “In Hetero Diels-Alder Methodology in Organic Synthesis,” Academic Press Inc., San Diego, 1987, p 239. [18] S. N. Mazumdar, M. Sharma and M. P. Mahajan, “Diels- Alder Cycloaddition Reactions of 1,3-Diazabutadienes with Sulfene,” Tetrahedron Letters, Vol. 28, No. 23, 1987, pp. 2641-2642. doi:10.1016/S0040-4039(00)96169-0 [19] P. Singh, G. Bhargava and M. P. Mahajan, “Tandem [2 + 2] Cycloaddition and Cope Rearrangement in Reactions of Cross-Conjugated Azatrienes with Conjugated Ketenes: A Facile Single Step Synthesis of Novel Azocinone Derivatives,” Tetrahedron, Vol. 62, No. 48, 2006, pp. 11267- 11273. doi:10.1016/j.tet.2006.09.007 [20] M. H. Elnagdi, S. M. Mousawi, M. M. Abdel-Khalik, S. El-Sheriny and E. John, “Studies with Enaminones: Reactivity of 1,5-Disubstituted-1,4-pentadien-3-ones toward Electrophilic Reagents. A Novel Route to Azolylazines, Benzofuranals, Pyranones,” Journal of Heterocyclic Chemistry, Vol. 38, No. 4, 2001, pp. 949-953. doi:10.1002/jhet.5570380422