Efficient Method for Tetrahydropyranylation of Phenols and Alcohols Using 2,4,6-Trichloro[1,3,5]triazine

Alcohols and phenols were tetrahydropyranylated in the presence of 2,4,6-trichloro[1,3,5]triazine in good to excellent yields in acetonitrile.

Anahtar Kelimeler:

2, 4, 6- Trichloro[1, 3, 5]triazine (TT), cyanuric chloride (CC), alcohol, phenol, tetrahydropyranylation, 3, 4-dihydro- 2H-pyran (DHP), protection

Efficient Method for Tetrahydropyranylation of Phenols and Alcohols Using 2,4,6-Trichloro[1,3,5]triazine

Alcohols and phenols were tetrahydropyranylated in the presence of 2,4,6-trichloro[1,3,5]triazine in good to excellent yields in acetonitrile.

Keywords:

2, 4, 6- Trichloro[1, 3, 5]triazine (TT), cyanuric chloride (CC), alcohol, phenol, tetrahydropyranylation, 3, 4-dihydro- 2H-pyran (DHP), protection,

PDF

___

T.W. Greene and P.G.M. Wuts, “Protective Groups in Organic Synthesis”, 3rd Ed. John Wiley: New York, 1999.
(a) E.J. Corey, H. Niwa and J. Knolle, J. Am. Chem. Soc. 100, 1942-43 (1978).
(b) K.F. Bernady, M.B. Floyd, J.F. Poletto and M.J. Weiss, J . Org. Chem. 44, 1438-47 (1979).
H. Alper and L. Dinkes, Synthesis 81-82 (1972).
M. Miyashita, A. Yoshikoshi and P.A. Grieco, J . Org. Chem, 42, 3772-74 (1977).
N. Rezai, F.A. Meybodi and P. Salehi, Synth. Commun. 30, 1799-05 (2000).
N. Deka and J.C. Sarma, Synth. Commun. 30, 4435-41 (2000).
M.A. Reddy, L.R. Reddy, N. Bhanumathi and K.R. Rao, Synth. Commun. 30, 4323- 28 (2000).
Y.S. Hon and C.F. Lee, Tetrahedron Lett. 40, 2389 (1999).
S. Naik, R. Gopinath and B.K. Patel, Tetrahedron Let. 42, 7679-81 (2001).
V.V. Namboodiri and R.S. Varma, Tetrahedron Lett. 43, 1143-46 (2002).
T. Mineno, Tetrahedron Lett. 43, 7975-7978 (2002).
V.V. Namboodiri and R.S. Varma, Chem. Commun. 342-3 (2002).
J.S. Yadav, B.V. Subba Reddy and D. Gnaneshwar, New J. Chem. 27, 202-4 (2003).
A.T. Khan, E. Mondal, B.M. Borah and S. Ghosh, Eur. J. Org. Chem. 21, 4113-17 (2003).
K. Venkataraman and D.R. Wagle, Tetrahedron Lett. 20, 3037-3040 (1979).
K. Venkataraman and D.R. Wagle, Tetrahedron Lett. 21, 1893-96 (1980).
M. Falorini, A. Porcheddu and M. Tadder, Tetrahedron Lett. 40, 4395-96 (1999).
D.C. Forbes, E.J. Barrett, D.L. Lewis and M.C. Smith, Tetrahedron Lett. 41, 9943-47 (2000).
M.S. Manhas, A.K. Bose and M.S. Khajavi, Synthesis 209-10 (1981).
G.A. Olah, A.P. Fung, B.G.B. Gupta and S.C. Narang, Synthesis 221 (1980).
L. De Luca, G. Giacomelli and A. Porcheddu, J . Org. Chem. 67, 5152-55 (2002).
L. De Luca, G. Giacomelli and A. Porcheddu, J . Org. Chem. 66,7907-09 (2001).
L. De Luca, G. Giacomelli and A. Porcheddu, Org. Lett. 4, 553-5 (2002).
B. Karimi, H. Hazarkhani and D. Zareyee, Synthesis 2513-16 (2002).
B. Akhlaghinia, M. Asadi, E. Safaei and M. Heydarpoor. J. Porphyrins and Phthalocyanies, 8, 1285 -88 (2004).
B. Akhlaghinia, M. Asadi, E. Safaei and M. Heydarpoor, Phosphorus, Sulfur and Silicon and the Related Elements 179, 2099-2104 (2004).
B. Akhlaghinia and S. Tavakoli, Synthesis 1775-78 (2005).
B. Akhlaghinia and E. Roohi, Lett. Org. Chem. 2, 725-730 (2005).
B. Akhlaghinia and E. Roohi, Lett. Org. Chem. 3, 220-224 (2006).