A Convenient Synthesis of 4,5-Disubstituted 1,2,4-Triazoles Functionalized in Position 3

Natalia V. Ivanova; Sergey I. Sviridov; Sergey V. Shorshnev; Aleksander E. Stepanov

doi:10.1055/s-2005-921754

PAPER

A Convenient Synthesis of 4,5-Disubstituted 1,2,4-Triazoles Functionalized in Position 3

Natalia V. Ivanova^a, Sergey I. Sviridov*^b, Sergey V. Shorshnev^b, Aleksander E. Stepanov^a
^a M. V. Lomonosov Moscow State Academy of Fine Chemical Technology, Malaya Pirogovskaya 1, 119435 Moscow, Russia
^b ChemBridge Corporation, Malaya Pirogovskaya 1, 119435 Moscow, Russia
Fax: +7(95)9564948; e-Mail: sviridov@chembridge.ru;

Abstract

All articles of this category

Abstract

A convenient approach to 4,5-disubstituted 3-hydroxymethyl-1,2,4-triazoles as well as to the corresponding 3-chloromethyl and 3-carboxaldehyde derivatives was developed starting from 3-mercapto-1,2,4-triazoles which can, in turn, be readily obtained from acyl hydrazines and isothiocyanates.

Key words

alcohols - aldehydes - heterocycles - oxidations - 1,2,4-triazoles

Full Text

References

1a Kakefuda A. Suzuki T. Tobe T. Tahara A. Sakamoto S. Tsukamoto S. Bioorg. Med. Chem. 2002, 10: 1905

1b Kurup A. Garg R. Carini DJ. Hansch C. Chem. Rev. 2001, 101: 2727

1c Meanwell NA. Rosenfeld MJ. Trehan AK. Romine JL. Wright JJK. Brassard CL. Buchanan JO. Federici ME. Fleming JS. J. Med. Chem. 1992, 35: 3498

2 1,2,4-Triazoles: Garratt PJ. Comprehensive Heterocyclic Chemistry II Vol. IV: Katritzky AR. Rees CW. Scriven EF. Pergamon; Oxford: 1995. p.127-163

3 Gall M. Hester JB. Rudzik AD. Lathi RA. J. Med. Chem. 1976, 19: 1057

4a Hoggarth A. J. Chem. Soc. 1949, 1163

4b Hoggarth A. J. Chem. Soc. 1950, 1579

5a Hester JB. VonVoigtlander P. Evenson GN. J. Med. Chem. 1980, 23: 873

5b Hester JB. J. Heterocycl. Chem. 1980, 17: 575

5c Martin A. Diaz JA. Vega S. An. Quim. 1995, 91: 3

6 Larsen SD. DiPaolo BA. Org. Lett. 2001, 3: 3341

7a Hester JB. Rudzik AD. VonVoigtlander P. J. Med. Chem. 1980, 23: 643

7b Gall M. Kamdar BV. Collins RJ. J. Med. Chem. 1978, 21: 1290

8 Robert-Piessard SC. Leger JM. Kumar P. Baut GL. Brion JD. J. Chem. Res., Miniprint 1989, 3: 511

9 Malbec F. Milcent R. Barbier G. J. Heterocycl. Chem. 1984, 21: 1689

10 Young O. J. Chem. Soc. 1901, 79: 668

11a Ismaiel AM. Yousif MY. Metwally MA. El-Kerdawy MM. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1984, 23: 489

11b Muhi-Eldeen Z. Nadir M. Aljobory NR. Husseen F. Stohs SJ. J. Med. Chem. Chim. Ther. 1991, 26: 237

11c Golovlyova SM. Moskvichev YA. Alov EM. Kobylinsky DB. Ermolaeva VV. Chem. Heterocycl. Compd. 2001, 37: 1102 ; Khim. Geterotsikl. Soedin. 2001, 37, 1201

12 Daunis E. Bull. Soc. Chim. Fr. 1971, 3296

13a Kubota E. J. Heterocycl. Chem. 1975, 12: 855

13b Metz HJ. Neunhoeffer H. Chem. Ber. 1982, 115: 2807

13c Horvath A. Tetrahedron Lett. 1996, 37: 4423

14a Pellizzari CH. Gazz. Chim. Ital. 1911, 41: 24

14b Boehringer S. inventors; US Patent, 1796403.

14c Ried L. Justus Liebigs Ann. Chem. 1966, 699: 88

14d Bany T. Rocz. Chem. 1968, 42: 247

14e Rao E. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1976, 14: 292

14f Nath TG. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1977, 15: 341

14g Stocks MJ. Cheshire DR. Reynolds R. Org. Lett. 2004, 6: 2969

15a Marckwald B. Chem. Ber. 1896, 29: 2916

15b Checchi R. Gazz. Chim. Ital. 1957, 87: 597

15c Fusco R. Ann. Chim. (Rome) 1960, 50: 277

15d Naqui S. . J. Sci. Ind. Res. Sect. B. 1962, 21: 195

15e Spassov A. Chem. Ber. 1966, 99: 3734

15f Spassov A. Demirov G. Chem. Ber. 1969, 102: 2530

15g Kevill P. Tetrahedron Lett. 1978, 4629

15h Ito S. Tanaka Y. Kakehi A. Bull. Chem. Soc. Jpn. 1984, 57: 544

15i