Literature DB >> 16494450

Thio acid/azide amidation: an improved route to N-acyl sulfonamides.

Kristin N Barlett1, Robert V Kolakowski, Sreenivas Katukojvala, Lawrence J Williams.   

Abstract

A one-pot procedure for the conversion of carboxylic acids to N-acyl sulfonamides, via thio acid/azide amidation, is presented. The method is compatible with acid- and base-sensitive amino acid protection. N-Acyl sulfonamide synthesis on solid support, peptide thio acid/sulfonazide coupling, and N-alkyl amide synthesis via selective cleavage of sulfonyl from an N-alkyl-N-acyl sulfonamide are also reported.

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Year:  2006        PMID: 16494450     DOI: 10.1021/ol052671d

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Dihydro-3-(triphenylphosphoranylidene)-2,5-thiophendione: A Convenient Synthon for the Preparation of Substituted 1,4-Thiazepin-5-ones and Piperidinones via the Intermediacy of Thioacids.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

2.  In situ carboxyl activation using a silatropic switch: a new approach to amide and peptide constructions.

Authors:  Wenting Wu; Zhihui Zhang; Lanny S Liebeskind
Journal:  J Am Chem Soc       Date:  2011-08-18       Impact factor: 15.419

3.  A Simple Method for the Conversion of Carboxylic Acids into Thioacids with Lawesson's Reagent.

Authors:  Yu Rao; Xuechen Li; Pavel Nagorny; Joji Hayashida; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-12-02       Impact factor: 2.415

4.  Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.

Authors:  David Crich; Kaname Sasaki
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

5.  Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry.

Authors:  David Crich; Kasinath Sana
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

7.  A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides.

Authors:  Markus Julian Schöwe; Odin Keiper; Carlo Unverzagt; Valentin Wittmann
Journal:  Chemistry       Date:  2019-11-07       Impact factor: 5.236

  7 in total

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