Literature DB >> 24437578

Intramolecular dearomatizing [3 + 2] annulation of α-imino carbenoids with aryl rings furnishing 3,4-fused indole skeletons.

Tomoya Miura1, Yuuta Funakoshi, Masahiro Murakami.   

Abstract

The rhodium-catalyzed dearomatizing [3 + 2] annulation reaction of 4-(3-arylpropyl)-1,2,3-triazoles is described. It provides a straightforward synthetic pathway from simple 5-aryl-1-alkynes leading to tricyclic 3,4-fused dihydroindoles via the corresponding 1,2,3-triazoles.

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Year:  2014        PMID： 24437578     DOI： 10.1021/ja412663a

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


  15 in total

1.  Rhodium-catalyzed NH insertion of pyridyl carbenes derived from pyridotriazoles: a general and efficient approach to 2-picolylamines and imidazo[1,5-a]pyridines.

Authors:  Yi Shi; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

2.  Expedient synthesis of fused azepine derivatives using a sequential rhodium(II)-catalyzed cyclopropanation/1-aza-Cope rearrangement of dienyltriazoles.

Authors:  Erica E Schultz; Vincent N G Lindsay; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-15       Impact factor: 15.336

3.  Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes.

Authors:  Jiajia Ma; Shuming Chen; Peter Bellotti; Renyu Guo; Felix Schäfer; Arne Heusler; Xiaolong Zhang; Constantin Daniliuc; M Kevin Brown; Kendall N Houk; Frank Glorius
Journal:  Science       Date:  2021-03-25       Impact factor: 47.728

4.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

5.  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

6.  Enantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.

Authors:  Robert W Kubiak; Jeffrey D Mighion; Sidney M Wilkerson-Hill; Joshua S Alford; Tetsushi Yoshidomi; Huw M L Davies
Journal:  Org Lett       Date:  2016-06-22       Impact factor: 6.005

7.  Synthesis of [3a,7a]-Dihydroindoles by a Tandem Arene Cyclopropanation/3,5-Sigmatropic Rearrangement Reaction.

Authors:  Sidney M Wilkerson-Hill; Brandon E Haines; Djamaladdin G Musaev; Huw M L Davies
Journal:  J Org Chem       Date:  2018-06-25       Impact factor: 4.354

8.  Catalytic Asymmetric Reactions of 4-Substituted Indoles with Nitroethene: A Direct Entry to Ergot Alkaloid Structures.

Authors:  Simone Romanini; Emilio Galletti; Lorenzo Caruana; Andrea Mazzanti; Fahmi Himo; Stefano Santoro; Mariafrancesca Fochi; Luca Bernardi
Journal:  Chemistry       Date:  2015-10-21       Impact factor: 5.236

9.  Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C-H bond insertion cascades.

Authors:  Jiun-Le Shih; Santa Jansone-Popova; Christopher Huynh; Jeremy A May
Journal:  Chem Sci       Date:  2017-09-04       Impact factor: 9.825

10.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

Authors:  Dongari Yadagiri; Pazhamalai Anbarasan
Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825
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