Highly Regioselective One‐Pot, Three‐Component Synthesis of 1‐Aryl‐3,4‐Substituted/Annulated‐5‐(Cycloamino)/(Alkylamino)pyrazoles from β‐Oxodithioesters
- 8 December 2011
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2012 (5) , 967-974
Abstract
An efficient, highly regioselective protocol for the synthesis of the title compounds is reported. The reaction involves a one‐pot, three‐component cyclocondensation of β‐oxodithioester, amine, and hydrazine in ethanol at reflux in the presence of a catalytic amount of acetic acid. Densely functionalized pyrazoles were constructed through the cyclization of a thioamide intermediate generated in situ from the β‐oxodithioester. This method allows a rapid and general synthesis of previously inaccessible pyrazoles and synthetically demanding pyrazoles containing fused rings.Keywords
This publication has 48 references indexed in Scilit:
- Rapid One-Pot, Four-Step Synthesis of Highly Fluorescent 1,3,4,5-Tetrasubstituted PyrazolesOrganic Letters, 2011
- Approaches towards the synthesis of 5-aminopyrazolesBeilstein Journal of Organic Chemistry, 2011
- Synthesis of pyrazolo[3,4‐b]pyridines using ammonium acetate as green reagent in multi‐component reactionsJournal of Heterocyclic Chemistry, 2008
- Base-Mediated Reaction of Hydrazones and Nitroolefins with a Reversed Regioselectivity: A Novel Synthesis of 1,3,4-Trisubstituted PyrazolesOrganic Letters, 2008
- Pyrazolo[1,5-a][1,3,5]triazines (5-Aza-9-deazapurines): Synthesis and Biological ActivityHETEROCYCLES, 2008
- Highly Regioselective Synthesis of 1-Aryl-3 (or 5)-alkyl/aryl-5 (or 3)-(N-cycloamino)pyrazolesThe Journal of Organic Chemistry, 2005
- New trends in the chemistry of 5‐aminopyrazolesJournal of Heterocyclic Chemistry, 2004
- Anilinopyrazole as selective CDK2 inhibitors: design, synthesis, biological evaluation, and x-ray crystallographic analysisBioorganic & Medicinal Chemistry Letters, 2003
- Sildenafil (VIAGRATM), a potent and selective inhibitor of type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunctionBioorganic & Medicinal Chemistry Letters, 1996
- A Facile One-Step Synthesis of Methyl β-OxodithiocarboxylatesSynthesis, 1982