Literature DB >> 15730325

Facile and highly selective conversion of nitriles to amides via indirect acid-catalyzed hydration using TFA or AcOH-H2SO4.

Jarugu Narasimha Moorthy1, Nidhi Singhal.   

Abstract

Both aliphatic and aromatic nitriles are conveniently and selectively converted in a single step, via an indirect acid-catalyzed hydration, into the corresponding amides in 1-8 h using a TFA-H2SO4 mixture as a reagent system. Although the same reagent did not work for the sterically hindered nitriles such as mesitonitrile, the transformation could be accomplished by changing TFA to AcOH at higher temperatures (>90 degrees C).

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Year:  2005        PMID: 15730325     DOI: 10.1021/jo048240a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

1.  Total syntheses and initial evaluation of [Ψ[C(═S)NH]Tpg⁴]vancomycin, [Ψ[C(═NH)NH]Tpg⁴]vancomycin, [Ψ[CH₂NH]Tpg⁴]vancomycin, and their (4-chlorobiphenyl)methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide antibiotics.

Authors:  Akinori Okano; Atsushi Nakayama; Kejia Wu; Erick A Lindsey; Alex W Schammel; Yiqing Feng; Karen C Collins; Dale L Boger
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

2.  Total synthesis of [Ψ[C(═S)NH]Tpg4]vancomycin aglycon, [Ψ[C(═NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors:  Jian Xie; Akinori Okano; Joshua G Pierce; Robert C James; Simon Stamm; Christine M Crane; Dale L Boger
Journal:  J Am Chem Soc       Date:  2012-01-06       Impact factor: 15.419

3.  Synthesis, physicochemical properties, and hydrogen bonding of 4(5)-substituted 1-H-imidazole-2-carboxamide, a potential universal reader for DNA sequencing by recognition tunneling.

Authors:  Feng Liang; Shengqing Li; Stuart Lindsay; Peiming Zhang
Journal:  Chemistry       Date:  2012-03-29       Impact factor: 5.236

Review 4.  Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

Authors:  Akinori Okano; Nicholas A Isley; Dale L Boger
Journal:  Chem Rev       Date:  2017-04-24       Impact factor: 60.622

5.  Preparation of Biomolecule-Polymer Conjugates by Grafting-From Using ATRP, RAFT, or ROMP.

Authors:  Marco S Messina; Kathryn M M Messina; Arvind Bhattacharya; Hayden R Montgomery; Heather D Maynard
Journal:  Prog Polym Sci       Date:  2019-11-18       Impact factor: 29.190

6.  8-Hydr-oxy-8-phenyl-2,3,7,8-tetra-hydro-6H-1,4-dioxino[2,3-f]isoindol-6-one.

Authors:  Viktor A Tafeenko; Leonid A Aslanov; Mahmud I Khasanov; Sergei S Mochalov
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-06

7.  Potent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: synthesis and SAR of novel analogs of MBX 1066 and MBX 1090.

Authors:  John D Williams; Son T Nguyen; Shen Gu; Xiaoyuan Ding; Michelle M Butler; Tommy F Tashjian; Timothy J Opperman; Rekha G Panchal; Sina Bavari; Norton P Peet; Donald T Moir; Terry L Bowlin
Journal:  Bioorg Med Chem       Date:  2013-10-25       Impact factor: 3.641

8.  2-(4-Chloro-phen-yl)acetamide.

Authors:  Dong-Sheng Ma; Pei-Jiang Liu; Shuai Zhang; Guang-Feng Hou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-12

9.  Crystal structure of 2-[4(E)-2,6-bis-(4-chloro-phen-yl)-3-ethyl-piperidin-4-yl-idene]acetamide.

Authors:  K Priya; K Saravanan; S Selvanayagam; S Kabilan
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-10-10

Review 10.  Recent advances in copper-catalyzed C-H bond amidation.

Authors:  Jie-Ping Wan; Yanfeng Jing
Journal:  Beilstein J Org Chem       Date:  2015-11-17       Impact factor: 2.883

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