Synthesis of Trifluoromethylated Pyrimido[1,2- b]indazole Derivatives through the Cyclocondensation of 3-Aminoindazoles with Ketoester and Their Functionalization via Suzuki-Miyaura Cross-Coupling and SNAr Reactions

Sakina Tellal; Badr Jismy; Djamila Hikem-Oukacha; Mohamed Abarbri

doi:10.3390/molecules29010044

Synthesis of Trifluoromethylated Pyrimido[1,2- b]indazole Derivatives through the Cyclocondensation of 3-Aminoindazoles with Ketoester and Their Functionalization via Suzuki-Miyaura Cross-Coupling and SN_Ar Reactions

Molecules. 2023 Dec 20;29(1):44. doi: 10.3390/molecules29010044.

Authors

Sakina Tellal^{1

2}, Badr Jismy¹, Djamila Hikem-Oukacha², Mohamed Abarbri¹

Affiliations

¹ Laboratoire de Physico-Chimie des Matériaux et des Electrolytes pour l'Energie (PCM2E), EA 6299, Avenue Monge Faculté des Sciences, Parc de Grandmont, 37200 Tours, France.
² Laboratory of Physics and Chemistry Materials LPCM, Department of Chemistry, Faculty of Sciences, University Mouloud Mammeri, Tizi-Ouzou 15000, Algeria.

Abstract

A new series of trifluoromethylated pyrimido[1,2-b]indazol-4(1H)-one derivatives was synthesized with good to excellent yields through a simple condensation of 3-aminoindazole derivatives with ethyl 4,4,4-trifluoro 3-oxobutanoate. The functionalization of the corresponding chlorinated fused tricyclic scaffolds via Suzuki-Miyaura and aromatic nucleophilic substitution reactions led to the synthesis of highly diverse trifluoromethylated pyrimido[1,2-b]indazole derivatives with good yields.

Keywords: 3-aminoindazole derivatives; SNAr; Suzuki-Miyaura cross-coupling; ethyl 4,4,4-trifluoro 3-oxobutanoate; trifluoromethylated pyrimido[1,2-b]indazole derivatives.

Grants and funding

This research received no external funding.