One-Pot Multicomponent Synthesis of Diversely Substituted 2-Aminopyrroles. A Short General Synthesis of Rigidins A, B, C, and D
Authors:
- 26 January 2011
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (5) , 1118-1121
Abstract
Privileged medicinal scaffolds based on the structures of tetra- and pentasubstituted 2-aminopyrroles were prepared via one-pot multicomponent reactions of structurally diverse aldehydes and N-(aryl-, hetaryl-, alkylsulfonamido)acetophenones with activated methylene compounds. This methodology was used in a four-step synthesis of alkaloids rigidins A, B, C, and D in overall yields of 61%, 58%, 60%, and 53%, respectively. Of these, rigidins B, C, and D were synthesized for the first time.Keywords
This publication has 61 references indexed in Scilit:
- Phospha-Münchnones: Electronic Structures and 1,3-Dipolar CycloadditionsThe Journal of Organic Chemistry, 2010
- Synthesis of Pyrroles by Consecutive Multicomponent Reaction/[4 + 1] Cycloaddition of α-Iminonitriles with IsocyanidesOrganic Letters, 2009
- Polyfunctional Nitriles in Organic Syntheses: A Novel Route to Aminopyrroles, Pyridazines and Pyrazolo[3,4-c]pyridazinesMolecules, 2009
- The Effect of 5-Alkyl Modification on the Biological Activity of Pyrrolo[2,3-d]pyrimidine Containing Classical and Nonclassical Antifolates as Inhibitors of Dihydrofolate Reductase and as Antitumor and/or Antiopportunistic Infection AgentsJournal of Medicinal Chemistry, 2008
- Palladium Catalyzed Synthesis of Münchnones from α‐Amidoethers: A Mild Route to PyrrolesAngewandte Chemie International Edition, 2008
- Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolinesBioorganic & Medicinal Chemistry Letters, 2008
- One‐Pot Three‐Component Catalytic Synthesis of Fully Substituted Pyrroles from Readily Available Propargylic Alcohols, 1,3‐Dicarbonyl Compounds and Primary AminesChemistry – A European Journal, 2007
- Adenosine Kinase Inhibitors. 6. Synthesis, Water Solubility, and Antinociceptive Activity of 5-Phenyl-7-(5-deoxy-β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidines Substituted at C4 with Glycinamides and Related CompoundsJournal of Medicinal Chemistry, 2005
- Design, Synthesis and Antiviral Activity of Novel 4,5-Disubstituted 7-(β-d-Ribofuranosyl)pyrrolo[2,3-d][1,2,3]triazines and the Novel 3-Amino-5-methyl-1-(β-d-ribofuranosyl)- and 3-Amino-5-methyl-1-(2-deoxy-β-d-ribofuranosyl)-1,5-dihydro-1,4,5,6,7,8-hexaazaacenaphthylene as Analogues of TriciribineJournal of Medicinal Chemistry, 2005
- Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moietiesIl Farmaco, 2002