Literature DB >> 14961694

N-Amination of pyrrole and indole heterocycles with monochloramine (NH2Cl).

John Hynes1, Wendel W Doubleday, Alaric J Dyckman, Jollie D Godfrey, John A Grosso, Susanne Kiau, Katerina Leftheris.   

Abstract

A survey of several electrophilic ammonia reagents for the N-amination of indole- and pyrrole-containing heterocycles revealed that monochloramine (NH(2)Cl) is an excellent reagent for this transformation. Pyrroles and indoles containing a variety of substitution were aminated on nitrogen with isolated yields ranging from 45% to 97%.

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Year:  2004        PMID： 14961694     DOI： 10.1021/jo035587p

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


  10 in total

1.  Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2015-07-14       Impact factor: 6.005

2.  Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors:  Erin D Anderson; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-07-19       Impact factor: 15.419

3.  Direct and Selective 3-Amidation of Indoles Using Electrophilic N-[(Benzenesulfonyl)oxy]amides.

Authors:  Gerardo X Ortiz; Brett N Hemric; Qiu Wang
Journal:  Org Lett       Date:  2017-03-10       Impact factor: 6.005

4.  Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution.

Authors:  Ryan E Quiñones; Zhi-Chen Wu; Dale L Boger
Journal:  J Org Chem       Date:  2021-09-09       Impact factor: 4.198

Review 5.  Control of asymmetry in the radical addition approach to chiral amine synthesis.

Authors:  Gregory K Friestad
Journal:  Top Curr Chem       Date:  2014

6.  Synthesis of pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones: Rearrangement of pyrrolo[1,2-d][1,3,4]oxadiazines and regioselective intramolecular cyclization of 1,2-biscarbamoyl-substituted 1H-pyrroles.

Authors:  Kkonnip Son; Seong Jun Park
Journal:  Beilstein J Org Chem       Date:  2016-08-09       Impact factor: 2.883

Review 7.  Facile and Scalable Methodology for the Pyrrolo[2,1-f][1,2,4]triazine of Remdesivir.

Authors:  Sarabindu Roy; Ajay Yadaw; Subho Roy; Gopal Sirasani; Aravind Gangu; Jack D Brown; Joseph D Armstrong; Rodger W Stringham; B Frank Gupton; Chris H Senanayake; David R Snead
Journal:  Org Process Res Dev       Date:  2022-01-07       Impact factor: 3.317

8.  Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Authors:  Timothy J Donohoe; Christopher R Jones; Anne F Kornahrens; Luiz C A Barbosa; Louise J Walport; Matthew R Tatton; Michael O'Hagan; Akshat H Rathi; David B Baker
Journal:  J Org Chem       Date:  2013-12-12       Impact factor: 4.354

9.  Expanding Access to Remdesivir via an Improved Pyrrolotriazine Synthesis: Supply Centered Synthesis.

Authors:  Dinesh J Paymode; Flavio S P Cardoso; Toolika Agrawal; John W Tomlin; Daniel W Cook; Justina M Burns; Rodger W Stringham; Joshua D Sieber; B Frank Gupton; David R Snead
Journal:  Org Lett       Date:  2020-09-15       Impact factor: 6.005

Review 10.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823
  10 in total

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