Desulfurization of Thioamides
into Amides with H2O2/ZrCl4 Reagent
System

Kiumars Bahrami; Mohammad Mehdi Khodaei; Yeganeh Tirandaz

doi:10.1055/s-0028-1083314

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2009(3): 369-371
DOI: 10.1055/s-0028-1083314

SHORTPAPER

Desulfurization of Thioamides into Amides with H₂O₂/ZrCl₄ Reagent System

Kiumars Bahrami*^a,b, Mohammad Mehdi Khodaei*^a,b, Yeganeh Tirandaz^a
^a Department of Chemistry, Razi University, Kermanshah 67149, Iran
^b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com; e-Mail: mmkhoda@razi.ac.ir;

Further Information

Publication History

Received 22 August 2008
Publication Date:
09 January 2009 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The hydrogen peroxide/zirconium(IV) chloride reagent system has been used as a new and efficient reagent for the deprotection/desulfurization of thioamides to amides. This system is reasonably general and can be applied to the conversion of several thioamides to the corresponding amides. The salient features of this protocol are short reaction times, good chemoselectivity, cleaner reaction profiles, and simple workup that precludes the use of toxic solvents.

Key words

deprotection - thioamides - amides - desulfurization - hydrogen peroxide

References

1 Shaabani A. Soleimani E. Rezayan AH. Tetrahedron Lett. 2007, 48: 6137

Crossref Google Scholar
2 Mohammadpoor-Baltork I. Khodaei MM. Nikoofar K. Tetrahedron Lett. 2003, 44: 591

Crossref Google Scholar
3 Mohammadpoor-Baltork I. Memarian HR. Hajipour AR. Bahrami K. Bull. Korean Chem. Soc. 2003, 24: 1002

Crossref Google Scholar
4 Mohammadpoor-Baltork I. Memarian HR. Bahrami K. Monatsh. Chem. 2002, 133: 189

Crossref Google Scholar
5 Movassagh B. Lakouraj MM. Ghodrati K. Synth. Commun. 2000, 30: 2353

Crossref Google Scholar
6 Masuda R. Hojo M. Ichi T. Sasano S. Kobayashi T. Kuroda C. Tetrahedron Lett. 1991, 32: 1195

Crossref Google Scholar
7a Kim HJ. Kim YH. Synthesis 1986, 970

Google Scholar
7b Rahman A.-U. Basha A. Waheed N. Tetrahedron Lett. 1976, 17: 219

Google Scholar
7c Tani J. Oine T. Inoue I. Synthesis 1975, 714

Google Scholar
8 Kochharl KS. Cottrell DA. Pinnick HW. Tetrahedron Lett. 1983, 24: 1323

Crossref Google Scholar
9 Mukherji P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1977, 15: 202

Google Scholar
10 Mikolajzyk M. Luczak J. Synthesis 1974, 491

Article in Thieme Connect Google Scholar
11 Mikolajzyk M. Luczak J. Synthesis 1975, 114

Article in Thieme Connect Google Scholar
12 Olah CA. Arvanaghi M. Ohannesian L. Surya PGK. Synthesis 1984, 785

Article in Thieme Connect Google Scholar
13 Mikolajzyk M. Luczak J. J. Org. Chem. 1978, 43: 2132

Crossref Google Scholar
14 Singh H. Singh P. Malhotra N. J. Chem. Soc., Perkin Trans. 1 1981, 2647

Crossref Google Scholar
15 Boudet R. Bull. Soc. Chim. Fr. 1951, 377

Google Scholar
16a Sato K. Aoki M. Noyori R. Science 1998, 281: 1646

Google Scholar
16b Brink GT. Arends IWC. Sheldon RA. Science 2000, 287: 1636

Google Scholar
17 Bahrami K. Tetrahedron Lett. 2006, 47: 2009

Crossref Google Scholar
18 Bahrami K. Khodaei MM. Kavianinia I. Synthesis 2007, 547

Article in Thieme Connect Google Scholar
19a Khodaei MM. Bahrami K. Karimi A. Synthesis 2008, 1682

Google Scholar
19b Bahrami K. Khodaei MM. Karimi A. Synthesis 2008, 2543

Google Scholar