Literature DB >> 16433505

The Neber route to substituted indoles.

Douglass F Taber1, Weiwei Tian.   

Abstract

Two complementary procedures have been developed for the conversion of the oximes of alpha-aryl ketones to azirines. On heating, the azirines rearrange smoothly to the corresponding indoles. The overall transformation offers a versatile route to indoles, complementary to the Fischer indole synthesis.

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Year:  2006        PMID： 16433505      PMCID： PMC3258442          DOI： 10.1021/ja058026j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

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Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

2.  Palladium-catalyzed tandem alkenyl and aryl C--N bond formation: a cascade N-annulation route to 1-functionalized indoles.

Authors:  Michael C Willis; Gareth N Brace; Ian P Holmes
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

3.  An annulative approach to highly substituted indoles: unusual effect of phenolic additives on the success of the arylation of ketone enolates.

Authors:  Jennifer L Rutherford; Matthew P Rainka; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2002-12-25       Impact factor: 15.419

4.  Photochemistry of 2-(1-naphthyl)-2H-azirines in matrixes and in solutions: wavelength-dependent C-C and C-N bond cleavage of the azirine ring.

Authors:  Hiroshi Inui; Shigeru Murata
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

5.  Synthesis of highly substituted indolines and indoles via intramolecular [4 + 2] cycloaddition of ynamides and conjugated enynes.

Authors:  Joshua R Dunetz; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

6.  Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin f from a single enantiomer of quinic Acid.

Authors:  Neil K Garg; Daniel D Caspi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-04-27       Impact factor: 15.419

7.  Synthesis of 5-substituted-1H-indol-2-yl-1H-quinolin-2-ones: a novel class of KDR kinase inhibitors.

Authors:  Jeffrey T Kuethe; Audrey Wong; Chuanxing Qu; Jacqueline Smitrovich; Ian W Davies; David L Hughes
Journal:  J Org Chem       Date:  2005-04-01       Impact factor: 4.354

8.  Discovery of 3-[(4,5,7-trifluorobenzothiazol-2-yl)methyl]indole-N-acetic acid (lidorestat) and congeners as highly potent and selective inhibitors of aldose reductase for treatment of chronic diabetic complications.

Authors:  Michael C Van Zandt; Michael L Jones; David E Gunn; Leo S Geraci; J Howard Jones; Diane R Sawicki; Janet Sredy; Jorge L Jacot; A Thomas Dicioccio; Tatiana Petrova; Andre Mitschler; Alberto D Podjarny
Journal:  J Med Chem       Date:  2005-05-05       Impact factor: 7.446

9.  Lipase-catalyzed resolution of (2R*,3S*)- and (2R*,3R*)-3-methyl-3-phenyl-2-aziridinemethanol at low temperatures and determination of the absolute configurations of the four stereoisomers.

Authors:  Takashi Sakai; Yu Liu; Hiroshi Ohta; Toshinobu Korenaga; Tadashi Ema
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

10.  Intramolecular C-N bond addition of amides to alkynes using platinum catalyst.

Authors:  Tomohiro Shimada; Itaru Nakamura; Yoshinori Yamamoto
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419
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  9 in total

1.  Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2H-azirines: synthesis of 2,3-disubstituted indoles.

Authors:  Samaresh Jana; Mack D Clements; Barry K Sharp; Nan Zheng
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

2.  Tandem Cycloisomerization/Suzuki Coupling of Arylethynyl MIDA Boronates.

Authors:  Julian M W Chan; Giovanni W Amarante; F Dean Toste
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

3.  Examination of the mechanism of Rh(2)(II)-catalyzed carbazole formation using intramolecular competition experiments.

Authors:  Benjamin J Stokes; Kathleen J Richert; Tom G Driver
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

4.  Rhodium-catalyzed intramolecular C-H insertion of alpha-aryl-alpha-diazo ketones.

Authors:  Douglass F Taber; Weiwei Tian
Journal:  J Org Chem       Date:  2007-03-27       Impact factor: 4.354

5.  A palladium-catalyzed Barluenga cross-coupling - reductive cyclization sequence to substituted indoles.

Authors:  S M Ashikur Rahman; Björn C G Söderberg
Journal:  Tetrahedron       Date:  2021-07-06       Impact factor: 2.388

6.  Transition Metal Free C-N Bond Forming Dearomatizations and Aryl C-H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent.

Authors:  Joshua J Farndon; Xiaofeng Ma; John F Bower
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

7.  Indole synthesis: a review and proposed classification.

Authors:  Douglass F Taber; Pavan K Tirunahari
Journal:  Tetrahedron       Date:  2011-09-23       Impact factor: 2.457

8.  Efficient access to enantiomerically pure cyclic alpha-amino esters through a lipase-catalyzed kinetic resolution.

Authors:  Sergio Alatorre-Santamaría; María Rodriguez-Mata; Vicente Gotor-Fernández; Marcos Carlos de Mattos; Francisco J Sayago; Ana I Jiménez; Carlos Cativiela; Vicente Gotor
Journal:  Tetrahedron Asymmetry       Date:  2009-01-25

9.  Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.

Authors:  Xianhai Tian; Lina Song; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-02       Impact factor: 15.336
  9 in total

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