Literature DB >> 21572597

Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Alison R Hardin Narayan1, Richmond Sarpong.   

Abstract

Hetero-cycloisomerization reactions of propargylic alcohol derivatives leading to indolizines have been demonstrated to proceed in the presence of water alone. This stands as a significant advance over the previous methods using Pt, Cu or Ag salts paired with ligands in organic solvents such as benzene, acetonitrile or methylene chloride.

Entities:  

Year:  2010        PMID: 21572597      PMCID: PMC3094017          DOI: 10.1039/C0GC00198H

Source DB:  PubMed          Journal:  Green Chem        ISSN: 1463-9262            Impact factor:   10.182


  22 in total

Review 1.  On inventing reactions for atom economy.

Authors:  Barry M Trost
Journal:  Acc Chem Res       Date:  2002-09       Impact factor: 22.384

2.  Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

3.  "On water": unique reactivity of organic compounds in aqueous suspension.

Authors:  Sridhar Narayan; John Muldoon; M G Finn; Valery V Fokin; Hartmuth C Kolb; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-20       Impact factor: 15.336

4.  Acceleration of organic reactions through aqueous solvent effects.

Authors:  Michael C Pirrung
Journal:  Chemistry       Date:  2006-02-01       Impact factor: 5.236

5.  Ga(III)-catalyzed cycloisomerization strategy for the synthesis of icetexane diterpenoids: total synthesis of (+/-)-salviasperanol.

Authors:  Eric M Simmons; Richmond Sarpong
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

6.  Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors:  B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

7.  Potent inhibitors of secretory phospholipase A2: synthesis and inhibitory activities of indolizine and indene derivatives.

Authors:  S Hagishita; M Yamada; K Shirahase; T Okada; Y Murakami; Y Ito; T Matsuura; M Wada; T Kato; M Ueno; Y Chikazawa; K Yamada; T Ono; I Teshirogi; M Ohtani
Journal:  J Med Chem       Date:  1996-09-13       Impact factor: 7.446

8.  Epoxide-opening cascades promoted by water.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Science       Date:  2007-08-31       Impact factor: 47.728

9.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Synthesis and antileukemic activity of bis[[(carbamoyl)oxy]methyl]- substituted pyrrolo[2,1-a]isoquinolines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isobenzazepines, and pyrrolo[1,2-a]benzazepines.

Authors:  W K Anderson; A R Heider; N Raju; J A Yucht
Journal:  J Med Chem       Date:  1988-11       Impact factor: 7.446

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  1 in total

1.  Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Authors:  Stephen T Heller; Toshihiro Kiho; Alison R H Narayan; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-05       Impact factor: 15.336

  1 in total

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