A Novel Approach to C-Trimethylsilyl-1,3-azoles

Evgenij V. Zarudnitskii; Igor I. Pervak; Anatolij S. Merkulov; Aleksandr A. Yurchenko; Andrej A. Tolmachev; Aleksandr M. Pinchuk

doi:10.1055/s-2006-926412

PAPER

A Novel Approach to C-Trimethylsilyl-1,3-azoles

Evgenij V. Zarudnitskii*^a, Igor I. Pervak^a, Anatolij S. Merkulov^a, Aleksandr A. Yurchenko^a, Andrej A. Tolmachev^b, Aleksandr M. Pinchuk^a
^a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska str. 5, 02094 Kiev, Ukraine
e-Mail: zhz@bpci.kiev.ua;
^b National Taras Shevchenko University, Volodymyrska str. 62, 01033 Kiev, Ukraine

Abstract

All articles of this category

Abstract

Direct silylation of 1,3-azoles with bromotrimethylsilane in the presence of triethylamine was investigated. 5-Phenyloxazole, benzoxazole, 1-methyl-1,2,4-triazole, 2-aryl-1,3,4-oxa- and thiadiazoles were found to give the corresponding 2- or 5-trimethylsilyl derivatives.

Key words

azoles - silylation - heterocycles - electrophilic substitution - silicon

Full Text

References

1 Lopyrev VA. Larina LI. Voronkov MG. Zh. Org. Khim. 2001, 37: 165 ; Russ. J. Org. Chem. (Engl. Transl.), 2001, 37, 149

2 Dondoni A. Synthesis 1998, 1681

3a Carpenter AJ. Chadwick DJ. Tetrahedron 1986, 42: 2351

3b Ngochindo RI. J. Chem. Soc., Perkin Trans. 1 1990, 1645

4a Pinkerton FH. Thames SF. J. Heterocycl. Chem. 1972, 9: 67

4b Dondoni A. Fantin G. Fogagnolo M. Medici A. Pedrini P. J. Org. Chem. 1988, 53: 1748

4c Pinkerton FH. Thames SF. J. Heterocycl. Chem. 1971, 8: 257

4d Anderson DK. Sikorski JA. Reitz DB. Pilla LT. J. Heterocycl. Chem. 1986, 23: 1257

5a Dondoni A. Fantin G. Fogagnolo M. Medici A. Pedrini P. J. Org. Chem. 1987, 52: 3413

5b Miller RA. Smith RM. Karady S. Reamer RA. Tetrahedron Lett. 2002, 43: 935

6a Frick U. Simchen G. Synthesis 1984, 929

6b Majchrzak MW. Simchen G. Tetrahedron 1986, 42: 1299

7 Begtrup M. Vedsø P. J. Chem. Soc., Perkin Trans. 1 1993, 625

8 Solé S. Gornitzka H. Guerret O. Bertrand G. J. Am. Chem. Soc. 1998, 120: 9100

9 Bassindale AR. Stout T. Tetrahedron Lett. 1985, 26: 3403

10a Belen’kii LI. Chuvylkin ND. Khim. Geterotsikl. Soedin. 1996, 32: 1535 ; Chem. Heterocycl. Compd. (Engl. Transl.) 1996, 32, 1319

11 Bourissou D. Guerret O. Gabbaï FP. Bertrand G. Chem. Rev. 2000, 100: 39

12 LaMattina JL. J. Org. Chem. 1980, 45: 2261

13 Saikachi H. Kitagawa T. Sasaki H. van Leusen AM. Chem. Pharm. Bull. 1979, 27: 793

14 Ainsworth C. J. Am. Chem. Soc. 1955, 77: 1148

15 Ainsworth C. J. Am. Chem. Soc. 1958, 80: 5201

16 Gaponik PN. Karavai VP. Grigor’ev YV. Khim. Geterotsikl. Soedin. 1985, 21: 1521

17 Ruppert I. Tetrahedron Lett. 1977, 1987