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A Novel Method for Synthesis of Tetrahydro-2H-oxazolo[2,3-a]isoquinolines
Corresponding Author(s) : K. Mantelingu
Asian Journal of Chemistry,
Vol. 31 No. 2 (2019): Vol. 31 No. 2
Abstract
An efficient and direct method for the synthesis of tetrahydro-2H-oxazolo[2,3-a]isoquinolines is reported. This novel method involves ®T3P mediated in situ oxidation of benzyl alcohols to aldehyde followed by acetic acid mediated [3+2] cycloaddition reaction to afford tetrahydro-2H-oxazolo[2,3- a]isoquinolines in one-pot operation with good to excellent yields. Heterocyclic alcohols also underwent the reaction with tetrahydroquinolines at room temperature
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- K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g.
- 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.
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References
X.W. Hong, Y.Q. Zhou, C.B. Bai, N.X. Wang, Y. Xing, W. Zhang, Y.J. Wang, X.W. Lan, Y. Xie and Y.H. Li, Molecules, 20, 17208 (2015); https://doi.org/10.3390/molecules200917208.
J. Alladoum, E. Vrancken, P. Mangeney, S. Roland and C. Kadouripuchot, Org. Lett., 11, 3746 (2009); https://doi.org/10.1021/ol901375w.
T. Nishitani, H. Shiraishi, S. Sakaguchi and Y. Ishii, Tetrahedron Lett., 41, 3389 (2000); https://doi.org/10.1016/S0040-4039(00)00374-9.
A. Chakraborty, S. Majumdar and D.K. Maiti, Tetrahedron Lett., 57, 3298 (2016); https://doi.org/10.1016/j.tetlet.2016.06.048.
D.S. Snyder, L. Tradtrantip, C. Yao, M.J. Kurth and A.S. Verkman, J. Med. Chem., 54, 5468 (2011); https://doi.org/10.1021/jm200505e.
G.W. Gribble and J.A. Joule, Progress in Heterocyclic Chemistry, Elsevier, vol. 27 (2015).
P.W. Ament, N. Jamshed and J.P. Horne, Am. Fam. Physician, 65, 663 (2002).
C. Wolf and H. Xu, Chem. Commun., 47, 3339 (2011); https://doi.org/10.1039/c0cc04629a.
N.C. Ghosal, S. Santra, G.V. Zyryanov, A. Hajra and A. Majee, Tetrahedron Lett., 57, 3551 (2016); https://doi.org/10.1016/j.tetlet.2016.06.119.
H. Firouzabadi, N. Iranpoor, A. Ghaderi and M. Ghavami, Tetrahedron Lett., 53, 5515 (2012); https://doi.org/10.1016/j.tetlet.2012.08.012.
M. Rahman, A.K. Bagdi, S. Mishra and A. Hajra, Chem. Commun., 50, 2951 (2014); https://doi.org/10.1039/c4cc00454j.
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.
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.
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.
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.
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.
K. Mantelingu, Y. Lin and D. Seidel, Org. Lett., 16, 5910 (2014); https://doi.org/10.1021/ol502918g.
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.
J.T.A. Vijay, N.K. Nandeesh, SC. Nagarakere, G.P. Suresha, R.S. Kanchugarakoppal and M. Kempegowda1, Cogent Chem., 1, 1 (2015); https://doi.org/10.1080/23312009.2015.1083068.