Literature DB >> 27378819

Synthesis of β-substituted tryptamines by regioselective ring opening of aziridines.

Jesse Kidd1, Kristen Maiden1, Jeremy B Morgan1.   

Abstract

Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce β-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

Entities:  

Keywords:  Aziridine; Indole; Regioselective; Ring opening; Tryptamine

Year:  2016        PMID： 27378819      PMCID： PMC4930112          DOI： 10.1016/j.tet.2016.03.031

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

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Authors:  S Lucarini; C Tomasini
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

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Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Phosphine-catalyzed Heine reaction.

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Journal:  Org Lett       Date:  2011-09-29       Impact factor: 6.005

4.  Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening.

Authors:  Hongqiang Liu; Vijaya R Pattabiraman; John C Vederas
Journal:  Org Lett       Date:  2007-09-12       Impact factor: 6.005

5.  The chemistry of transition metals with three-membered ring heterocycles.

Authors:  Chung-Yang Dennis Huang; Abigail G Doyle
Journal:  Chem Rev       Date:  2014-05-28       Impact factor: 60.622

Review 6.  Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.

Authors:  Anna J Kochanowska-Karamyan; Mark T Hamann
Journal:  Chem Rev       Date:  2010-08-11       Impact factor: 60.622

7.  Synthesis of 1,2-trans-2-acetamido-2-deoxyhomoiminosugars.

Authors:  Yves Blériot; Anh Tuan Tran; Giuseppe Prencipe; Yerri Jagadeesh; Nicolas Auberger; Sha Zhu; Charles Gauthier; Yongmin Zhang; Jérôme Désiré; Isao Adachi; Atsushi Kato; Matthieu Sollogoub
Journal:  Org Lett       Date:  2014-10-20       Impact factor: 6.005

8.  Ring opening of pymisyl-protected aziridines with organocuprates.

Authors:  Jan Bornholdt; Jakob Felding; Rasmus P Clausen; Jesper L Kristensen
Journal:  Chemistry       Date:  2010-11-02       Impact factor: 5.236

9.  Solid supported chemical syntheses of both components of the lantibiotic lacticin 3147.

Authors:  Wei Liu; Alice S H Chan; Hongqiang Liu; Stephen A Cochrane; John C Vederas
Journal:  J Am Chem Soc       Date:  2011-08-17       Impact factor: 15.419

10.  Synthetic indole and melatonin derivatives exhibit antimalarial activity on the cell cycle of the human malaria parasite Plasmodium falciparum.

Authors:  Desirée C Schuck; Alessandro K Jordão; Myna Nakabashi; Anna C Cunha; Vitor F Ferreira; Célia R S Garcia
Journal:  Eur J Med Chem       Date:  2014-03-18       Impact factor: 6.514
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  2 in total

Review 1.  Nucleophilic ring opening reactions of aziridines.

Authors:  Rabia Akhtar; Syed Ali Raza Naqvi; Ameer Fawad Zahoor; Sameera Saleem
Journal:  Mol Divers       Date:  2018-05-04       Impact factor: 2.943

2.  A practical method for the aziridination of α,β-unsaturated carbonyl compounds with a simple carbamate utilizing sodium hypochlorite pentahydrate.

Authors:  Takehiro Umeda; Satoshi Minakata
Journal:  RSC Adv       Date:  2021-06-22       Impact factor: 3.361
  2 in total

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