Literature DB >> 24998910

Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides.

Joshua S Alford1, Huw M L Davies.   

Abstract

An effective method for aminoacylation of indoles and pyrroles has been achieved. The transformation involves a multicomponent one-pot cascade reaction between indoles or pyrroles, ynol ethers, and sulfonyl azides, creating four different bonds regioselectively through N-sulfonyltriazole intermediates. The oxo-tryptamines and oxo-pyrroloethanamines are generated in moderate to high yields under mild reaction conditions.

Entities:  

Year:  2014        PMID： 24998910     DOI： 10.1021/ja5058967

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


  10 in total

1.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

2.  Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

Authors:  John M Bennett; Jonathan D Shapiro; Krystina N Choinski; Yingbin Mei; Sky M Aulita; Giovanny M Dominguez; Max M Majireck
Journal:  J Vis Exp       Date:  2018-01-03       Impact factor: 1.355

3.  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

4.  Rh(I)/Sc(OTf)3-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones.

Authors:  Qinghua Wei; Zi Li; Xi Yang; Jianghui Chen; Xiaohua Liu; Wenhao Hu; Shunying Liu
Journal:  Mol Divers       Date:  2019-04-05       Impact factor: 2.943

Review 5.  Recent advances in the application of indoles in multicomponent reactions.

Authors:  Ghodsi Mohammadi Ziarani; Razieh Moradi; Tahereh Ahmadi; Negar Lashgari
Journal:  RSC Adv       Date:  2018-03-28       Impact factor: 4.036

6.  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

7.  Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure.

Authors:  Guofeng Li; Man Zhao; Junqiu Xie; Ying Yao; Lingyun Mou; Xiaowei Zhang; Xiaomin Guo; Wangsheng Sun; Zheng Wang; Jiecheng Xu; Jianzhong Xue; Tao Hu; Ming Zhang; Min Li; Liang Hong
Journal:  Chem Sci       Date:  2020-03-13       Impact factor: 9.825

8.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

9.  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

10.  Chemical Consequences of the Mechanical Bond: A Tandem Active Template-Rearrangement Reaction.

Authors:  Florian Modicom; Ellen M G Jamieson; Elise Rochette; Stephen M Goldup
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-14       Impact factor: 15.336
  10 in total

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