An Efficient Novel Synthesis of Hydroxy- and Alkoxysultams Using MMPP as Oxidant of Isothiazolium Salts

Kathleen Taubert; Anja Siegemund; Alexander Eilfeld; Sven Baumann; Joachim Sieler; Bärbel Schulze

doi:10.1055/s-2003-42087

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Synthesis 2003(14): 2265-2268
DOI: 10.1055/s-2003-42087

SPECIALTOPIC

An Efficient Novel Synthesis of Hydroxy- and Alkoxysultams Using MMPP as Oxidant of Isothiazolium Salts

Kathleen Taubert^a, Anja Siegemund^a, Alexander Eilfeld^a, Sven Baumann^a, Joachim Sieler^b, Bärbel Schulze*^a
^a Institut für Organische Chemie, Fakultät für Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: bschulze@organik.chemie.uni-leipzig.de;
^b Institut für Anorganische Chemie, Fakultät für Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, Germany

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Publication History

Received 15 August 2003
Publication Date:
24 September 2003 (online)

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Abstract

The oxidation reaction of isothiazolium salts 6 with magnesium monoperoxyphthalate (MMPP) in ethanol or water in the ultrasound bath affords new 3-hydroxysultams 10 and 3-alkoxysultams 15 in very high yields. A HPLC-API-MS(MS) method was used for monitoring of the oxidation of salts 6 with MMPP.

Key words

sultams - oxidation - magnesium monoperoxyphthalate (MMPP) - hydroperoxides

References

1 De A. Prog. Med. Chem. 1981, 18: 117

Search in Google Scholar
2 Schulze B. Illgen K. J. Prakt. Chem. 1997, 339: 1

Crossref Search in Google Scholar
3 Taubert K. Kraus S. Schulze B. Sulfur Reports 2002, 23: 79

Crossref Search in Google Scholar
4 Siegemund A. Taubert K. Schulze B. Sulfur Reports 2002, 23: 279

Crossref Search in Google Scholar
5 Davis M. Adv. Heterocycl. Chem. 1985, 38: 105

Search in Google Scholar
6 Burri KF. Helv. Chim. Acta 1989, 72: 1416

Crossref Search in Google Scholar
7 Abou-Gharbia M. Moyer JA. Patel U. Webb M. Schiehser G. Andree T. Haskins JT. J. Med. Chem. 1989, 23: 1024

Search in Google Scholar
8 Schulze B. Kirsten G. Kirrbach S. Rahm A. Heimgärtner H. Helv. Chim. Acta 1991, 74: 1059

Search in Google Scholar
9a Marco JL. Ingate ST. Tetrahedron Lett. 1997, 38: 4835

Crossref Search in Google Scholar
9b Ingate ST. Marco JL. Witvrouw M. Pennecouque C. De Clerq E. Tetrahedron 1997, 53: 17795

Crossref Search in Google Scholar
9c Marco JL. Ingate ST. Tetrahedron Lett. 1998, 39: 4123

Crossref Search in Google Scholar
9d Marco JL. Ingate ST. Chinon PM. Tetrahedron 1999, 55: 7625

Crossref Search in Google Scholar
9e Marco JL. Ingate ST. Jaime C. Bea J. Tetrahedron 2000, 56: 2523

Crossref Search in Google Scholar
10 Fischer R, Kretschik O, Schenke T, Schenkel R, Wiedemann J, Erdelen C, Loesel P, Drewes MW, Feucht D, and Andersch W. inventors; Ger. Offen. DE 1999244668. ; Chem. Abstr. 2001, 134, 4932
11 Hanson PR. Probst DA. Robinson RE. Yan M. Tetrahedron Lett. 1999, 40: 4761

Crossref Search in Google Scholar
12 Ho KF. Fung DCW. Wong WY. Chan WH. Lee AWM. Tetrahedron Lett. 2001, 42: 3121

Crossref Search in Google Scholar
13 Wanner J. Harned AM. Probst DA. Poon KWC. Klein TA. Snelgrove KA. Hanson PR. Tetrahedron Lett. 2002, 43: 917

Crossref Search in Google Scholar
14 Taubert K. Sieler J. Hennig L. Findeisen M. Schulze B. Helv. Chim. Acta 2002, 85: 183

Crossref Search in Google Scholar
15 Gelalcha FG. Schulze B. J. Org. Chem. 2002, 67: 8400

Crossref Search in Google Scholar
16 Baumann S. Möder M. Herzschuh R. Schulze B. Chromatographia 2003, 57: S147

Search in Google Scholar
17 Gütschow M. Pietsch M. Taubert K. Freysoldt THE. Schulze B. Z. Naturforsch., B: Chem. Sci. 2003, 58: 111

Search in Google Scholar
18 Armstrong A. Barsanti PA. Clarke PA. Wood A. J. Chem. Soc., Perkin Trans. 1 1996, 1373

Crossref
19 Schulze B. Taubert K. Gelalcha FG. Hartung C. Sieler J. Z. Naturforsch., B: Chem. Sci. 2002, 57: 383

Search in Google Scholar
21 Sheldrick GM. Acta Cryst. 1990, 46: 467

Crossref Search in Google Scholar
22 Sheldrick GM. SHELXL-97, Program for the refinement of crystal structures Göttingen; Germany: 1997.

20

Crystals were obtained from acetone. The intensities were measured on a Siemens SMART CCD diffractometer. Data collection and cell refinement are listed in the text. The structure was solved by direct methods with SHELX-97. [21] The refinement was done with SHELXL-97. [22] Crystallographic data for the structural analyses have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 217553 for 15f. Copies of the data can be obtained, free of charge, from CCDC, 12 Union Road, Cambridge, CB2 1EZ. UK (fax:+44(1233)336033; e-mail: deposit@ccdc.cam.ac.uk; internet: http://www.ccdc.cam.ac.uk).