Efficient Trimethylsilylation and Tetrahydropyranylation of Alcohols in the Presence of 1,3-Dibromo-5,5-dimethylhydantoin

Farhad Shirini; Mohammad Ali Zolfigol; Maryam Paktinat

doi:10.1055/s-2006-950350

PAPER

Efficient Trimethylsilylation and Tetrahydropyranylation of Alcohols in the Presence of 1,3-Dibromo-5,5-dimethylhydantoin

Farhad Shirini*^a, Mohammad Ali Zolfigol^b, Maryam Paktinat^a
^a Department of Chemistry, College of Science, Guilan University, Rasht 41335, Iran
Fax: +98(131)3220066; e-Mail: shirini@guilan.ac.ir;
^b Department of Chemistry, College of Science, Bu-Ali Sina University, Hamadan 65174, Iran
e-Mail: zolfi@basu.ac.ir;

Abstract

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Abstract

Chemoselective trimethylsilylation and tetrahydropyranylation of benzylic and primary and secondary aliphatic alcohols proceed efficiently in the presence of 1,3-dibromo-5,5-dimethylhydantoin (DBH) under mild and completely heterogeneous reaction conditions in excellent yields.

Key words

alcohols - 1,3-dibromo-5,5-dimethylhydantoin - trimethylsilylation - tetrahydropyranylation - heterogeneous reaction conditions

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Referenzen

References

1a Pinnick WH. Bal BS. Lajis NH. Tetrahedron Lett. 1978, 4261

1b Morita T. Okomoto Y. Sakuti H. Tetrahedron Lett. 1980, 21: 835

1c Olah G. Husain H. Gupta BGB. Salem GF. Narang SD. J. Org. Chem. 1981, 46: 5212

1d Amantini D. Fringuelli F. Pizzo P. Vaccaro L. J. Org. Chem. 2001, 66: 6743

2a Cossy J. Pale P. Tetrahedron Lett. 1978, 6093

2b Tarkelson S. Anisworth C. Synthesis 1976, 722

3 Bruynes CA. Jurrines TK. J. Org. Chem. 1982, 47: 3966

4a Zhang ZH. Li TS. Yang F. Fu CG. Synth. Commun. 1998, 28: 305

4b Curini M. Epifano F. Marcotullio MC. Rosati O. Constantino U. Synth. Commun. 1999, 29: 541

4c Firouzabadi H. Iranpoor N. Amani K. Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002, 2601

4d Karimi B. Golshani B. J. Org. Chem. 2000, 65: 7228

4e Khazaei A. Zolfigol MA. Rostami A. Ghorbani CA. Catal. Commun. 2006, in press

4f Shirini F. Zolfigol MA. Mohammadi K. Phosphorous, Sulfur Silicon Relat. Elem. 2003, 178: 1567

4g Shirini F. Zolfigol MA. Abedini M. Bull. Chem. Soc. Jpn. 2005, 78: 1982

5a Jones RG. Mann MJ. J. Am. Chem. Soc. 1953, 75: 4048

5b Miyashita M. Yoshikoshi A. Grieco PA. J. Org. Chem. 1977, 42: 3772

6a Ogawa Y. Shibasaki M. Tetrahedron Lett. 1984, 25: 663

6b Namboodiri VV. Varma RS. Tetrahedron Lett. 2002, 43: 1143

7 Ravindranath N. Ramesh C. Das B. Synlett 2001, 1777

8 Rezai N. Meybodi FA. Salehi P. Synth. Commun. 2000, 30: 1799

9 Karimi B. Khalkhali M. J. Mol. Catal. A: Chem. 2005, 232: 113

10 Karimi B. Maleki J. Tetrahedron Lett. 2002, 43: 5353

11 Keh CCK. Namboodiri VV. Varma RS. Li CJ. Tetrahedron Lett. 2002, 43: 4993

12 Pore DM. Desai UV. Mane RB. Wadgaonkar PP. Synth. Commun. 2004, 34: 2135

13 Firouzabadi H. Iranpoor N. Hazarkhani H. Synth. Commun. 2004, 34: 3623

14 Habibi MH. Tangestaninejad S. Mohammadpoor-Baltork I. Mirkhani V. Yadollahi B. Tetrahedron Lett. 2001, 42: 2851

15 Kumar P. Dinesh CV. Reddy RS. Pandey B. Synthesis 1993, 1069

16a Shirini F. Zolfigol MA. Mollarazi E. Lett. Org. Chem. 2005, 2: 718

16b Zolfigol MA. Azarifar D. Maleki B. Tetrahedron Lett. 2004, 45: 2181

16c Zolfigol MA. Shirini F. Ghorbani CA. Synthesis 2006, 2043

17 Zolfigol MA. Ghaemi E. Madrakian E. Ghorbani CA. Mendeleev Commun. 2006, 41

18 Azarifar D. Zolfigol MA. Maleki B. Bull. Korean Chem. Soc. 2004, 25: 1

19 Alam A. Takaguchi Y. Stuboi S. Synth. Commun. 2005, 35: 1329

20 Zolfigol MA. Nasr-Isfahani H. Mallakpour S. Safaiee M. Synthesis 2005, 761

21 Zolfigol MA. Khazaei A. Ghorbani CA. Rostami A. Hajjami M. Catal. Commun. 2006, 7: 399