Literature DB >> 18937414

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

Isabelle Bouillon1, Jaroslav Zajícek, Nadĕzda Pudelová, Viktor Krchnák.   

Abstract

Base-catalyzed tandem carbon-carbon followed by nitrogen-nitrogen bond formations quantitatively converted N-alkyl-2-nitro-N-(2-oxo-2-aryl-ethyl)-benzenesulfonamides to 2H-indazoles 1-oxides under mild conditions. Triphenylphosphine or mesyl chloride/triethylamine-mediated deoxygenation afforded 2H-indazoles.

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Year:  2008        PMID： 18937414      PMCID： PMC2653199          DOI： 10.1021/jo8018895

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


  24 in total

1.  Syntheses of potent, selective, and orally bioavailable indazole-pyridine series of protein kinase B/Akt inhibitors with reduced hypotension.

Authors:  Gui-Dong Zhu; Viraj B Gandhi; Jianchun Gong; Sheela Thomas; Keith W Woods; Xiaohong Song; Tongmei Li; R Bruce Diebold; Yan Luo; Xuesong Liu; Ran Guan; Vered Klinghofer; Eric F Johnson; Jennifer Bouska; Amanda Olson; Kennan C Marsh; Vincent S Stoll; Mulugeta Mamo; James Polakowski; Thomas J Campbell; Ruth L Martin; Gary A Gintant; Thomas D Penning; Qun Li; Saul H Rosenberg; Vincent L Giranda
Journal:  J Med Chem       Date:  2007-05-25       Impact factor: 7.446

2.  GdCl(3) catalysed Grieco condensation: a facile approach for the synthesis of novel pyrimidine and annulated pyrimidine fused indazole derivatives in single pot under mild conditions and their anti-microbial activity.

Authors:  T Yakaiah; B P V Lingaiah; B Narsaiah; K Pranay Kumar; U S N Murthy
Journal:  Eur J Med Chem       Date:  2007-04-14       Impact factor: 6.514

3.  Anticancer mechanisms of YC-1 in human lung cancer cell line, NCI-H226.

Authors:  Chun-Jen Chen; Mei-Hua Hsu; Li-Jiau Huang; Takao Yamori; Jing-Gung Chung; Fang-Yu Lee; Che-Ming Teng; Sheng-Chu Kuo
Journal:  Biochem Pharmacol       Date:  2007-08-17       Impact factor: 5.858

4.  Discovery of novel indazole-linked triazoles as antifungal agents.

Authors:  Joon Seok Park; Kyung A Yu; Tae Hee Kang; Sunghoon Kim; Young-Ger Suh
Journal:  Bioorg Med Chem Lett       Date:  2007-03-27       Impact factor: 2.823

5.  p-alkoxybenzyl alcohol resin and p-alkoxybenzyloxycarbonylhydrazide resin for solid phase synthesis of protected peptide fragments.

Authors:  S S Wang
Journal:  J Am Chem Soc       Date:  1973-02-21       Impact factor: 15.419

6.  Synthesis and biological evaluation of 3,5-diaminoindazoles as cyclin-dependent kinase inhibitors.

Authors:  Jinho Lee; Hwangeun Choi; Kyoung-Hee Kim; Shinwu Jeong; Jong-Wook Park; Chul-Su Baek; Sei-Hee Lee
Journal:  Bioorg Med Chem Lett       Date:  2008-03-06       Impact factor: 2.823

7.  Activities of 7-nitroindazole and 1-(2-(trifluoromethylphenyl)-imidazole independent of neuronal nitric-oxide synthase inhibition.

Authors:  Nobuko Matsumura; Kazue Kikuchi-Utsumi; Toshio Nakaki
Journal:  J Pharmacol Exp Ther       Date:  2008-02-12       Impact factor: 4.030

8.  Gamendazole, an orally active indazole carboxylic acid male contraceptive agent, targets HSP90AB1 (HSP90BETA) and EEF1A1 (eEF1A), and stimulates Il1a transcription in rat Sertoli cells.

Authors:  Joseph S Tash; Ramappa Chakrasali; Sudhakar R Jakkaraj; Jennifer Hughes; S Kendall Smith; Kaori Hornbaker; Leslie L Heckert; Sedide B Ozturk; M Kyle Hadden; Terri Goss Kinzy; Brian S J Blagg; Gunda I Georg
Journal:  Biol Reprod       Date:  2008-01-23       Impact factor: 4.285

9.  Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists.

Authors:  Itsuro Shimada; Kyoichi Maeno; Ken-ichi Kazuta; Hideki Kubota; Tetsuya Kimizuka; Yasuharu Kimura; Ken-ichi Hatanaka; Yuki Naitou; Fumikazu Wanibuchi; Shuichi Sakamoto; Shin-ichi Tsukamoto
Journal:  Bioorg Med Chem       Date:  2007-11-04       Impact factor: 3.641

10.  Use of trichloroacetimidate linker in solid-phase Peptide synthesis.

Authors:  Liang Zeng Yan; John P Mayer
Journal:  J Org Chem       Date:  2003-02-07       Impact factor: 4.354
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  6 in total

1.  Synthesis of quinazolines from N-(2-nitrophenylsulfonyl)iminodiacetate and alpha-(2-nitrophenylsulfonyl)amino ketones via 2H-indazole 1-oxides.

Authors:  Sona Krupková; Greg A Slough; Viktor Krchnák
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354

2.  Unprecedented rearrangement of 2-(2-aminoethyl)-1-aryl-3,4-dihydropyrazino[1,2-b]indazole-2-ium 6-oxides to 2,3-dihydro-1H-imidazo[1,2-b]indazoles.

Authors:  Jan Kocí; Allen G Oliver; Viktor Krchnák
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

3.  Solid-phase synthesis and chemical properties of 2-(2-amino/hydroxyethyl)-1-aryl-3,4-dihydropyrazino[1, 2-b]indazol-2-iums.

Authors:  Jan Kocí; Viktor Krchnák
Journal:  J Comb Chem       Date:  2010 Jan-Feb

4.  Polymer-supported alpha-acylamino ketones: preparation and application in syntheses of 1,2,4-trisubstituted-1H-imidazoles.

Authors:  Jan Kocí; Nadĕzda Pudelová; Viktor Krchnák
Journal:  J Comb Chem       Date:  2009 May-Jun

5.  Multiplicity of diverse heterocycles from polymer-supported alpha-acylamino ketones.

Authors:  Nadezda Pudelová; Viktor Krchnák
Journal:  J Comb Chem       Date:  2009 Sep-Oct

6.  Efficient traceless solid-phase synthesis of 3,4-dihydropyrazino[1,2-b]indazoles and their 6-oxides.

Authors:  Nadezda Pudelová; Viktor Krchnák
Journal:  J Comb Chem       Date:  2009 May-Jun
  6 in total

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