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Novel Synthesis of Hexahydrochromeno[4,3-b]pyrrolo[2,1-a]isoquinolines via C-H Functionalization
Corresponding Author(s) : K. Mantelingu
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
In present work, an efficient and direct method for the synthesis of hexahydrochromeno[4,3-b]pyrrolo[2,1-a]isoquinolines is reported. This method involves ®T3P mediated oxidation of alcohols to aldehydes followed by [3+2] cycloaddition to afford hexahydrochromeno[4,3-b]pyrrolo[2,1-a]isoquinolines with good yields.
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- M.L. Bolognesi, V. Andrisano, M. Bartolini, A. Minarini, M. Rosini, V. Tumiatti and C. Melchiorre, J. Med. Chem., 44, 105 (2001); https://doi.org/10.1021/jm000991r.
- M. Facompré, C. Tardy, C. Bal-Mahieu, P. Colson, I. Manzanares, C. Perez, C. Cuevas and C. Bailly, Cancer Res., 63, 7392 (2003).
- D. Pla, F. Albericio and M. Alvarez, Anticancer. Agents Med. Chem., 8, 746 (2008); https://doi.org/10.2174/187152008785914789.
- E.G. Baggiolini, H.L. Lee, G. Pizzolato and M.R. Uskokovic, J. Am. Chem. Soc., 104, 6460 (1982); https://doi.org/10.1021/ja00387a057.
- K.V. Gothelf and K.A. Jørgensen, Chem. Rev., 98, 863 (1998); https://doi.org/10.1021/cr970324e.
- K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g.
- P.N. Confalone and E.M. Huie, J. Am. Chem. Soc., 106, 7175 (1984); https://doi.org/10.1021/ja00335a051.
- R. Grigg, G. Donegan, H.Q.N. Gunaratne, D.A. Kennedy, J.F. Malone, V. Sridharan and S. Thianpatanagul, Tetrahedron, 45, 1723 (1989); https://doi.org/10.1016/S0040-4020(01)80037-5.
- V.S. Moshkin, V.Y. Sosnovskikh and G.V. Röschenthaler, Tetrahedron, 69, 5884 (2013); https://doi.org/10.1016/j.tet.2013.05.018.
- B.B. Snider, Y. Ahn and B.M. Foxman, Tetrahedron Lett., 40, 3339 (1999); https://doi.org/10.1016/S0040-4039(99)00461-X.
- N. Basavaprabhu, N. Narendra, R.S. Lamani and V.V. Sureshbabu, Tetrahedron Lett., 51, 3002 (2010); https://doi.org/10.1016/j.tetlet.2010.04.002.
- F.L. Zumpe, M. Flüß, K. Schmitz and A. Lender, Tetrahedron Lett., 48, 1421 (2007); https://doi.org/10.1016/j.tetlet.2006.12.098.
- A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 95 (2013); https://doi.org/10.1016/j.tetlet.2012.10.112.
- T.A. Jenifer Vijay, K.N. Nandeesh, G.M. Raghavendra, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 6533 (2013); https://doi.org/10.1016/j.tetlet.2013.09.094.
- T.A.J. Vijay, K.N. Nandeesh, N.C. Sandya, G.P. Suresha, K.S. Rangappa and K. Manteligu, Cogent Chem., 1, 1083068 (2015); https://doi.org/10.1080/23312009.2015.1083068.
- G.M. Raghavendra, A.B. Ramesha, C.N. Revanna, K.N. Nandeesh, K. Mantelingu and K.S. Rangappa, Tetrahedron Lett., 52, 5571 (2011); https://doi.org/10.1016/j.tetlet.2011.08.037.
- K.B. Mantelingu, M.P. Sadashiva and K. S. Rangappa, Indian J. Chem., 43B, 1954 (2004).
- C.S. Pavan Kumar, K.B. Harsha, N.C. Sandhya, A.B. Ramesha, K. Mantelingu and K.S. Rangappa, New J. Chem., 39, 8397 (2015); https://doi.org/10.1039/C5NJ01706H.
- C.N. Revanna, G.M. Raghavendra, K.N. Nandeesh, D.G. Bhadregowda, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 5224 (2013); https://doi.org/10.1016/j.tetlet.2013.07.076.
- C.S. Pavan Kumar, K.B. Harsha, K. Mantelingu and K.S. Rangappa, RSC Adv., 5, 61664 (2015); https://doi.org/10.1039/C5RA10030E.
References
M.L. Bolognesi, V. Andrisano, M. Bartolini, A. Minarini, M. Rosini, V. Tumiatti and C. Melchiorre, J. Med. Chem., 44, 105 (2001); https://doi.org/10.1021/jm000991r.
M. Facompré, C. Tardy, C. Bal-Mahieu, P. Colson, I. Manzanares, C. Perez, C. Cuevas and C. Bailly, Cancer Res., 63, 7392 (2003).
D. Pla, F. Albericio and M. Alvarez, Anticancer. Agents Med. Chem., 8, 746 (2008); https://doi.org/10.2174/187152008785914789.
E.G. Baggiolini, H.L. Lee, G. Pizzolato and M.R. Uskokovic, J. Am. Chem. Soc., 104, 6460 (1982); https://doi.org/10.1021/ja00387a057.
K.V. Gothelf and K.A. Jørgensen, Chem. Rev., 98, 863 (1998); https://doi.org/10.1021/cr970324e.
K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g.
P.N. Confalone and E.M. Huie, J. Am. Chem. Soc., 106, 7175 (1984); https://doi.org/10.1021/ja00335a051.
R. Grigg, G. Donegan, H.Q.N. Gunaratne, D.A. Kennedy, J.F. Malone, V. Sridharan and S. Thianpatanagul, Tetrahedron, 45, 1723 (1989); https://doi.org/10.1016/S0040-4020(01)80037-5.
V.S. Moshkin, V.Y. Sosnovskikh and G.V. Röschenthaler, Tetrahedron, 69, 5884 (2013); https://doi.org/10.1016/j.tet.2013.05.018.
B.B. Snider, Y. Ahn and B.M. Foxman, Tetrahedron Lett., 40, 3339 (1999); https://doi.org/10.1016/S0040-4039(99)00461-X.
N. Basavaprabhu, N. Narendra, R.S. Lamani and V.V. Sureshbabu, Tetrahedron Lett., 51, 3002 (2010); https://doi.org/10.1016/j.tetlet.2010.04.002.
F.L. Zumpe, M. Flüß, K. Schmitz and A. Lender, Tetrahedron Lett., 48, 1421 (2007); https://doi.org/10.1016/j.tetlet.2006.12.098.
A.B. Ramesha, G.M. Raghavendra, K.N. Nandeesh, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 95 (2013); https://doi.org/10.1016/j.tetlet.2012.10.112.
T.A. Jenifer Vijay, K.N. Nandeesh, G.M. Raghavendra, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 6533 (2013); https://doi.org/10.1016/j.tetlet.2013.09.094.
T.A.J. Vijay, K.N. Nandeesh, N.C. Sandya, G.P. Suresha, K.S. Rangappa and K. Manteligu, Cogent Chem., 1, 1083068 (2015); https://doi.org/10.1080/23312009.2015.1083068.
G.M. Raghavendra, A.B. Ramesha, C.N. Revanna, K.N. Nandeesh, K. Mantelingu and K.S. Rangappa, Tetrahedron Lett., 52, 5571 (2011); https://doi.org/10.1016/j.tetlet.2011.08.037.
K.B. Mantelingu, M.P. Sadashiva and K. S. Rangappa, Indian J. Chem., 43B, 1954 (2004).
C.S. Pavan Kumar, K.B. Harsha, N.C. Sandhya, A.B. Ramesha, K. Mantelingu and K.S. Rangappa, New J. Chem., 39, 8397 (2015); https://doi.org/10.1039/C5NJ01706H.
C.N. Revanna, G.M. Raghavendra, K.N. Nandeesh, D.G. Bhadregowda, K.S. Rangappa and K. Mantelingu, Tetrahedron Lett., 54, 5224 (2013); https://doi.org/10.1016/j.tetlet.2013.07.076.
C.S. Pavan Kumar, K.B. Harsha, K. Mantelingu and K.S. Rangappa, RSC Adv., 5, 61664 (2015); https://doi.org/10.1039/C5RA10030E.