Literature DB >> 20681598

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

Samaresh Jana1, Mack D Clements, Barry K Sharp, Nan Zheng.   

Abstract

A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl(2)-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO(2), OMe, CF(3), OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.

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Year:  2010        PMID： 20681598      PMCID： PMC2955291          DOI： 10.1021/ol101130e

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


  17 in total

Review 1.  Practical methodologies for the synthesis of indoles.

Authors:  Guy R Humphrey; Jeffrey T Kuethe
Journal:  Chem Rev       Date:  2006-07       Impact factor: 60.622

2.  The Neber route to substituted indoles.

Authors:  Douglass F Taber; Weiwei Tian
Journal:  J Am Chem Soc       Date:  2006-02-01       Impact factor: 15.419

Review 3.  Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

Authors:  Kazuhiro Higuchi; Tomomi Kawasaki
Journal:  Nat Prod Rep       Date:  2007-03-23       Impact factor: 13.423

4.  Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by Pd(II)-catalyzed C-H activation reactions.

Authors:  Jiao-Jie Li; Tian-Sheng Mei; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Synthesis of indoles via domino reaction of N-aryl amides and ethyl diazoacetate.

Authors:  Sun-Liang Cui; Jing Wang; Yan-Guang Wang
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

6.  Palladium-catalyzed amination of aromatic C-H bonds with oxime esters.

Authors:  Yichen Tan; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

7.  Synthesis of N-substituted indole derivatives via PIFA-mediated intramolecular cyclization.

Authors:  Yunfei Du; Renhe Liu; Gregory Linn; Kang Zhao
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

8.  Indoles from simple anilines and alkynes: palladium-catalyzed C-H activation using dioxygen as the oxidant.

Authors:  Zhuangzhi Shi; Chun Zhang; Si Li; Delin Pan; Shengtao Ding; Yuxin Cui; Ning Jiao
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Inhibitors of human immunodeficiency virus type 1 (HIV-1) attachment. 5. An evolution from indole to azaindoles leading to the discovery of 1-(4-benzoylpiperazin-1-yl)-2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (BMS-488043), a drug candidate that demonstrates antiviral activity in HIV-1-infected subjects.

Authors:  Tao Wang; Zhiwei Yin; Zhongxing Zhang; John A Bender; Zhong Yang; Graham Johnson; Zheng Yang; Lisa M Zadjura; Celia J D'Arienzo; Dawn DiGiugno Parker; Christophe Gesenberg; Gregory A Yamanaka; Yi-Fei Gong; Hsu-Tso Ho; Hua Fang; Nannan Zhou; Brian V McAuliffe; Betsy J Eggers; Li Fan; Beata Nowicka-Sans; Ira B Dicker; Qi Gao; Richard J Colonno; Pin-Fang Lin; Nicholas A Meanwell; John F Kadow
Journal:  J Med Chem       Date:  2009-12-10       Impact factor: 7.446

10.  Simple conversion of enamines to 2H-azirines and their rearrangements under thermal conditions.

Authors:  Xiaoxun Li; Yunfei Du; Zhidan Liang; Xiangke Li; Yan Pan; Kang Zhao
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005
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  7 in total

1.  Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

2.  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

3.  Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-12-03       Impact factor: 4.354

4.  A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles.

Authors:  Soumitra Maity; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336

5.  Iron(II) bromide-catalyzed intramolecular C-H bond amination [1,2]-shift tandem reactions of aryl azides.

Authors:  Quyen Nguyen; Tuyen Nguyen; Tom G Driver
Journal:  J Am Chem Soc       Date:  2013-01-03       Impact factor: 15.419

6.  Investigation on the reactivity of α-azidochalcones with carboxylic acids: Formation of α-amido-1,3-diketones and highly substituted 2-(trifluoromethyl)oxazoles.

Authors:  Kandasamy Rajaguru; Arumugam Mariappan; Rajendran Suresh; Periasamy Manivannan; Shanmugam Muthusubramanian
Journal:  Beilstein J Org Chem       Date:  2015-10-29       Impact factor: 2.883

7.  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
  7 in total

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