Literature DB >> 16311805

Alternative method of Boc-removal from sulfamide using silica-phenyl sulfonic acid in conjunction with microwave heating.

Shahnaz Ghassemi1, Kristin Fuchs.   

Abstract

A general method was used to prepare an array of unsymmetric sulfamides. This was accomplished by the stepwise addition of CSI to tert-butanol followed by the addition of amines. To increase diversity, nitrogen group of Boc-sulfamides was alkylated with alcohols using Mitsunobu reaction and Boc-group was removed using Si-TsOH. Microwave heating was used in all the steps. The final sulfamides were released from Si-TsOH using NH3 in MeOH.

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Year:  2005        PMID: 16311805     DOI: 10.1007/s11030-005-7456-z

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  7 in total

1.  N-(tert-butoxycarbonyl)-N-[4-(dimethylazaniumylidene)-1,4-dihydropyridin-1-ylsulfonyl]azanide: a new sulfamyolating agent. Structure and reactivity toward amines.

Authors:  J Y Winum; L Toupet; V Barragan; G Dewynter; J L Montero
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

2.  Synthesis of a sulfahydantoin library.

Authors:  F Albericio; L M Bryman; J Garcia; E L Michelotti; E Nicolás; C M Tice
Journal:  J Comb Chem       Date:  2001 May-Jun

3.  Highly selective synthesis of heterosubstituted aromatic sulfamides.

Authors:  F Hof; P M Iovine; D W Johnson; J Rebek
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

4.  Relationships between structure and interaction kinetics for HIV-1 protease inhibitors.

Authors:  Per-Olof Markgren; Wesley Schaal; Markku Hämäläinen; Anders Karlén; Anders Hallberg; Bertil Samuelsson; U Helena Danielson
Journal:  J Med Chem       Date:  2002-12-05       Impact factor: 7.446

5.  Nonnucleoside human cytomegalovirus inhibitors: synthesis and antiviral evaluation of (chlorophenylmethyl)benzothiadiazine dioxide derivatives.

Authors:  A Martinez; C Gil; C Perez; A Castro; C Prieto; J Otero; G Andrei; R Snoeck; J Balzarini; E De Clercq
Journal:  J Med Chem       Date:  2000-08-24       Impact factor: 7.446

6.  Synthesis and comparative molecular field analysis (CoMFA) of symmetric and nonsymmetric cyclic sulfamide HIV-1 protease inhibitors.

Authors:  W Schaal; A Karlsson; G Ahlsén; J Lindberg; H O Andersson; U H Danielson; B Classon; T Unge; B Samuelsson; J Hultén; A Hallberg; A Karlén
Journal:  J Med Chem       Date:  2001-01-18       Impact factor: 7.446

7.  Novel N-aryl and N-heteroaryl sulfamide synthesis via palladium cross coupling.

Authors:  Lilian Alcaraz; Colin Bennion; James Morris; Premji Meghani; Stephen M Thom
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

  7 in total
  1 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

  1 in total

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