Literature DB >> 18229936

A practical, metal-free synthesis of 1H-indazoles.

Carla M Counceller1, Chad C Eichman, Brenda C Wray, James P Stambuli.   

Abstract

The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0-23 degrees C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.

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Year:  2008        PMID: 18229936     DOI: 10.1021/ol800053f

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


  5 in total

1.  Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.

Authors:  Benjamin J Stokes; Carl V Vogel; Linda K Urnezis; Minjie Pan; Tom G Driver
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

2.  Synthesis of fused indazole ring systems and application to nigeglanine hydrobromide.

Authors:  Aaron C Sather; Orion B Berryman; Julius Rebek
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

3.  Remarkably efficient synthesis of 2H-indazole 1-oxides and 2H-indazoles via tandem carbon-carbon followed by nitrogen-nitrogen bond formation.

Authors:  Isabelle Bouillon; Jaroslav Zajícek; Nadĕzda Pudelová; Viktor Krchnák
Journal:  J Org Chem       Date:  2008-10-21       Impact factor: 4.354

4.  N-N bond-forming cyclization for the one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines.

Authors:  Lindsay E Evans; Matthew D Cheeseman; Keith Jones
Journal:  Org Lett       Date:  2012-06-26       Impact factor: 6.005

Review 5.  Synthetic strategy and structure-activity relationship (SAR) studies of 3-(5'-hydroxymethyl-2'-furyl)-1-benzyl indazole (YC-1, Lificiguat): a review.

Authors:  Ko-Hua Yu; Hsin-Yi Hung
Journal:  RSC Adv       Date:  2021-12-20       Impact factor: 3.361

  5 in total

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