Literature DB >> 19618957

Indazoles: regioselective protection and subsequent amine coupling reactions.

David J Slade1, Nicholas F Pelz, Wanda Bodnar, John W Lampe, Paul S Watson.   

Abstract

Indazoles are unselectively protected under strongly basic conditions to give a mixture at N-1 and N-2. Under mildly acidic conditions, regioselective protection at N-2 takes place. Thermodynamic conditions lead to regioselective protection at N-1. This trend applies to various substituted indazoles. Protected 5-bromoindazoles participate in Buchwald reactions with a range of amines to generate novel derivatives.

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Year:  2009        PMID： 19618957     DOI： 10.1021/jo9006656

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


  6 in total

1.  Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors:  Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

2.  Efficient Pd-catalyzed amination reactions for heterocycle functionalization.

Authors:  Jaclyn L Henderson; Stephen L Buchwald
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

Authors:  Gary A Molander; DaWeon Ryu; Mona Hosseini-Sarvari; Rammohan Devulapally; Dave G Seapy
Journal:  J Org Chem       Date:  2013-06-25       Impact factor: 4.354

4.  Copper-Catalyzed Cross-Coupling of Benzylic C-H Bonds and Azoles with Controlled N-Site Selectivity.

Authors:  Si-Jie Chen; Dung L Golden; Shane W Krska; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2021-08-31       Impact factor: 16.383

5.  Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction.

Authors:  Manjunatha Narayanarao; Lokesh Koodlur; Vijayakumar G Revanasiddappa; Subramanya Gopal; Susmita Kamila
Journal:  Beilstein J Org Chem       Date:  2016-12-29       Impact factor: 2.883

6.  The Suzuki reaction applied to the synthesis of novel pyrrolyl and thiophenyl indazoles.

Authors:  Antonella Migliorini; Chiara Oliviero; Tecla Gasperi; Maria Antonietta Loreto
Journal:  Molecules       Date:  2012-04-16       Impact factor: 4.411
  6 in total

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