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Literature DB >> 19719195

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

Abstract

Thiocarboxylates, prepared conveniently by cleavage of 9-fluorenylmethyl or trimethoxybenzyl thioesters, react at room temperature with isocyanates and isothiocyanates to give amide bonds in good to excellent yield. A carboxylate salt is also shown to react with an electron-deficient isocyanate to give the corresponding amide in excellent yield at room temperature.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19719195 PMCID： PMC2739115 DOI： 10.1021/ol901370y

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

24 in total

Review 1. Emerging methods in amide- and peptide-bond formation.

Authors: Jeffery W Bode
Journal: Curr Opin Drug Discov Devel Date: 2006-11

2. Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

Authors: Per Restorp; Julius Rebek
Journal: J Am Chem Soc Date: 2008-08-13 Impact factor: 15.419

3. Chemical synthesis of alpha-inhibin-92 by the thiocarboxyl segment coupling method.

Authors: J Blake; D Yamashiro; K Ramasharma; C H Li
Journal: Int J Pept Protein Res Date: 1986-11

4. New segment synthesis of alpha-inhibin-92 by the acyl disulfide method.

Authors: D Yamashiro; C H Li
Journal: Int J Pept Protein Res Date: 1988-03

5. Thio-alpha-amino acids (S-acids) as a carboxyl component in peptide synthesis catalysed by papain.

Authors: N P Zapevalova
Journal: Int J Pept Protein Res Date: 1990-04

6. Resin-bound sulfonyl azides: efficient loading and activation strategy for the preparation of the N-acyl sulfonamide linker.

Authors: Remco Merkx; Matthijs J van Haren; Dirk T S Rijkers; Rob M J Liskamp
Journal: J Org Chem Date: 2007-05-12 Impact factor: 4.354

7. One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides.

Authors: David Crich; Kaname Sasaki; Md Yeajur Rahaman; Albert A Bowers
Journal: J Org Chem Date: 2009-05-15 Impact factor: 4.354

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

Authors: Kristin N Barlett; Robert V Kolakowski; Sreenivas Katukojvala; Lawrence J Williams
Journal: Org Lett Date: 2006-03-02 Impact factor: 6.005

9. Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides.

Authors: David Crich; Kasinath Sana; Songpo Guo
Journal: Org Lett Date: 2007-09-27 Impact factor: 6.005

10. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

Authors: Ning Shangguan; Sreenivas Katukojvala; Rachel Greenberg; Lawrence J Williams
Journal: J Am Chem Soc Date: 2003-07-02 Impact factor: 15.419

11 in total

1. Facile amide formation via S-nitrosothioacids.

Authors: Jia Pan; Nelmi O Devarie-Baez; Ming Xian
Journal: Org Lett Date: 2011-01-27 Impact factor: 6.005

2. Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.

Authors: Harsha Amarasekara; David Crich
Journal: Carbohydr Res Date: 2016-10-08 Impact factor: 2.104

3. 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

Review 4. Rethinking amide bond synthesis.

Authors: Vijaya R Pattabiraman; Jeffrey W Bode
Journal: Nature Date: 2011-12-21 Impact factor: 49.962

5. Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors: Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2015-10-01 Impact factor: 15.419

6. The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.

Authors: Appi Reddy Mandhapati; Salla Rajender; Jonathan Shaw; David Crich
Journal: Angew Chem Int Ed Engl Date: 2014-11-28 Impact factor: 15.336