Literature DB >> 22163373

An interrupted Ugi reaction enables the preparation of substituted indoxyls and aminoindoles.

John S Schneekloth1, Jimin Kim, Erik J Sorensen.   

Abstract

In a variation of the classical Ugi reaction, an acid promoted reaction between imines and isocyanides forms both 3-aminoindoles and substituted indoxyls. A recently reported triflyl phosphoramide is shown to be critical to obtain high yields under mild conditions.

Entities:  

Year:  2009        PMID： 22163373      PMCID： PMC3230264          DOI： 10.1016/j.tet.2008.08.055

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


  10 in total

1.  Polymer-supported glyoxylate and alpha-imino acetates. Versatile reagents for the synthesis of alpha-hydroxycarboxylic acid and alpha-amino acid libraries.

Authors:  S Kobayashi; R Akiyama; H Kitagawa
Journal:  J Comb Chem       Date:  2001 Mar-Apr

2.  Multicomponent Reactions with Isocyanides.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-09-15       Impact factor: 15.336

3.  Catalytic Asymmetric Hetero-Diels-Alder Reactions of Carbonyl Compounds and Imines.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-16       Impact factor: 15.336

Review 4.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

5.  Asymmetric Brønsted acid catalysis: enantioselective nucleophilic substitutions and 1,4-additions.

Authors:  Magnus Rueping; Boris J Nachtsheim; Stefan A Moreth; Michael Bolte
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  A new reaction of nitriles; amides from alkenes and mononitriles.

Authors:  J J RITTER; P P MINIERI
Journal:  J Am Chem Soc       Date:  1948-12       Impact factor: 15.419

7.  A new reaction of nitriles; synthesis of t-carbinamines.

Authors:  J J RITTER; J KALISH
Journal:  J Am Chem Soc       Date:  1948-12       Impact factor: 15.419

8.  Synthesis of 11-hydroxyl O-methylsterigmatocystin and the role of a cytochrome P-450 in the final step of aflatoxin biosynthesis.

Authors:  Daniel W Udwary; Linda K Casillas; Craig A Townsend
Journal:  J Am Chem Soc       Date:  2002-05-15       Impact factor: 15.419

9.  Synthesis of novel heterocyclic structures via reaction of isocyanides with S-trans-enones.

Authors:  Jeffrey D Winkler; Sylvie M Asselin
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

10.  Multicomponent reactions with dihydroazines: efficient synthesis of a diverse set of pyrido-fused tetrahydroquinolines.

Authors:  Inés Carranco; José Luis Díaz; Oscar Jiménez; Marc Vendrell; Fernando Albericio; Miriam Royo; Rodolfo Lavilla
Journal:  J Comb Chem       Date:  2005 Jan-Feb
  10 in total
  4 in total

1.  Indole synthesis: a review and proposed classification.

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

2.  A chemical synthesis of 11-methoxy mitragynine pseudoindoxyl featuring the interrupted Ugi reaction.

Authors:  Jimin Kim; John S Schneekloth; Erik J Sorensen
Journal:  Chem Sci       Date:  2012-09-01       Impact factor: 9.825

3.  Studies on the interaction of isocyanides with imines: reaction scope and mechanistic variations.

Authors:  Ouldouz Ghashghaei; Consiglia Annamaria Manna; Esther Vicente-García; Marc Revés; Rodolfo Lavilla
Journal:  Beilstein J Org Chem       Date:  2014-01-06       Impact factor: 2.883

Review 4.  Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles.

Authors:  András Váradi; Travis C Palmer; Rebecca Notis Dardashti; Susruta Majumdar
Journal:  Molecules       Date:  2015-12-23       Impact factor: 4.411
  4 in total

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