Efficient deprotection of Boc group in amines and sulfamides using Dawson heteropolyacid catalyst | European Journal of Chemistry

Default Image

PDF

Published: Sep 30, 2012

DOI: https://doi.org/10.5155/eurjchem.3.3.305-309.610

Keywords:

Catalyst, Cyclosulfamides, Protective group, N-Boc deprotection, Dawson heteropolyacid, Heterogeneous catalysis

Section

Research Article

Issue

Vol. 3 No. 3 (2012): September 2012

Dates

Received 2012-04-07
Accepted 2012-05-19
Published 2012-09-30

Roubila Belghiche

eMail

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria

Zinelaabidine Cheraiet

eMail

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria

Malika Berredjem

eMail

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria

Mostefa Abbessi

eMail

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria

Nour-Eddine Aouf

eMail

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar Annaba University, 23000, Algeria

Abstract

A series of sulfamides containing two protecting groups have been synthesized starting from N-benzoylaminoacids derivatives of (glycine, alanine, valine, leucine, phenylalanine), chlorosulfonylisocyanate and primary amines. Selective deprotection of the cyclic or linear sulfamides and amines has been achieved by treatment with heteropolyacid, which is easily recoverable and reusable. This method represents a reasonable alternative to the previous reported deprotection procedures.

3_3_305_309_800

This Abstract was viewed 2613 times |

Article PDF downloaded 11683 times

How to Cite

(1)

Belghiche, R.; Cheraiet, Z.; Berredjem, M.; Abbessi, M.; Aouf, N.-E. Efficient Deprotection of Boc Group in Amines and Sulfamides Using Dawson Heteropolyacid Catalyst. Eur. J. Chem. 2012, 3, 305-309.

Share

Links for Article

Crossref - Scopus - Google - European PMC

Crossref

Scopus

Google Scholar

Europe PMC

References

[1]. Greene, T. W.; Wuts, P. G. Protective Group in Organic Synthesis, 4rd Edition, John Wiley, New York, 2007.

[2]. Kocienski, P. J. In Protecting Group, Georges ThiemeVerlag, Stuttgart, 2004.

[3]. Hassa, I.; Marnelli, E. R.; Lin, L. C.; Fowler, F. W.; Levy, A. B. J. Org. Chem. 1981, 46, 157-162.
http://dx.doi.org/10.1021/jo00314a034

[4]. Rawal, R. J.; Jones, M. P.; Cava, K. J. Org. Chem.1987, 52, 19-24.
http://dx.doi.org/10.1021/jo00377a004

[5]. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465-468.
http://dx.doi.org/10.1016/S0040-4039(00)86862-8

[6]. Slaikh, N. S.; Gajare, A. S.; Deshpande, V. H.; Bedekar, A. V. Tetrahedron Lett. 2000, 41, 385-387.
http://dx.doi.org/10.1016/S0040-4039(99)02028-6

[7]. Apelqvist, T.; Wensbo, D. Tetrahedron Lett. 1996, 37, 1471-1472.
http://dx.doi.org/10.1016/0040-4039(95)02398-4

[8]. Klai, N.; Berredjem, M.; Khettache, N.; Belghit, M. Y.; Regainia, Z.; Aouf, N. J. Heterocycl. Chem. 2004, 41, 57-60.
http://dx.doi.org/10.1002/jhet.5570410109

[9]. Cheraiet, Z.; Ouarna, S.; Jamel, Z.; Berredjem, M.; Aouf, N. Inter. J. Chem. 2012, 4(3), 73-79.

[10]. Cheraiet, Z.; Ouarna, S.; Hessainia, S.; Berredjem, M.; Aouf, N. ISRN Org. Chem. 2012, 404235, 1-8.
http://dx.doi.org/10.5402/2012/404235

[11]. Kozhevnikov, I.V. J. Mol. Catal. A: Chem. 2009, 305, 1-2, 104-111.

[12]. Day W.; Klemperer, W. G. Science. 1985, 228, 533-538.
http://dx.doi.org/10.1126/science.228.4699.533
PMid:17736064

[13]. Keita, B.; Abdeldjalil, E.; Nadjo, L.; Avisse, B.; Contant, R.; Canny, J.; Richet, M. Electrochem. Comm. 2000, 2, 145-149.
http://dx.doi.org/10.1016/S1388-2481(99)00165-4

[14]. Romanelli, G. T.; Autino, J. C.; Baronetti, G.; Thomas, H. J. Molecules 2001, 6, 1006-1011.
http://dx.doi.org/10.3390/61201006

[15]. Romanelli, G.; Autino, J. C.; Baronetti, G.; Thomas, H. J. Tetrahedron Lett. 2002, 43, 7589-7591.
http://dx.doi.org/10.1016/S0040-4039(02)01822-1

[16]. Romanelli, G.; Thomas, H. J.; Querini, C. A. Appl. Catal. 2001, 217, 131-141.
http://dx.doi.org/10.1016/S0926-860X(01)00576-2

[17]. Heravi, M. M.; Bakhtiari, K.; Bamoharram, F. F.; Tehrani, M. H. Monatsh. Chem. 2007, 138, 465-467.
http://dx.doi.org/10.1007/s00706-007-0594-5

[18]. Kishore, P. S.; Viswanathan, B.; Varadarajan, T. K. Tetrahedron Lett. 2006, 47, 429-431.
http://dx.doi.org/10.1016/j.tetlet.2005.11.079

[19]. Romaneli, G. P.; Bennardi, D. O.; Autino, J. C.; Baronetti, G.; Thomas, G. T. E-Journal of Chemistry. 2008, 5, 641-647.
http://dx.doi.org/10.1155/2008/945898

[20]. Heydari, A.; Shiroodi, R. K.; Hamadi, H.; Esfandyari, M.; Pourayoubi, M. Tetrahedron Lett. 2007, 48, 5865-5868.
http://dx.doi.org/10.1016/j.tetlet.2007.06.064

[21]. Dewynter, G., Aouf, N.; Criton, M.; Montero, J. L. Tetrahedron. 1993, 49, 65-76.
http://dx.doi.org/10.1016/S0040-4020(01)80506-8

[22]. Aouf, N.; Dewynter, G.; Montero, J. L. Tettrahedron Lett. 1991, 32, 6545-6546.
http://dx.doi.org/10.1016/0040-4039(91)80216-S

[23]. Dewynter, G.; Aouf, N.; Regainia, Z.; Montero, J. L. Tetrahedron 1996, 52, 993-1004.
http://dx.doi.org/10.1016/0040-4020(95)00932-9

[24]. Baronetti, G. T.; Briand, L.; Sedran, U.; Thomas, H. Appl. Catal. A. 1998, 172, 265-272.
http://dx.doi.org/10.1016/S0926-860X(98)00134-3

[25]. Regainia, Z.; Abdaoui, M.; Aouf, N.; Dewynter, G.; Montero, J. L. Tetrahedron. 2000, 56, 381-387.
http://dx.doi.org/10.1016/S0040-4020(99)01025-X

[26]. Bendjeddou, A.; Berredjem, M.; Hattab, Z.; Regainia, Z.; Aouf, N. Phosphorus Sulfur. 2006, 181, 1351-1356.
http://dx.doi.org/10.1080/10426500500327014

[27]. Wang, G.; Li, C.; Jia, X. Tetrahedron Lett. 2009, 50, 1438-1440.
http://dx.doi.org/10.1016/j.tetlet.2009.01.056

Supporting Agencies

Algerian Ministry of Scientific Research (Direction Générale de la Recherche Scientifique et du Développement Technologique, DGRS-DT)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).