Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp2)-H Bond Selenylation of Imidazo[2,1- b]thiazole and Related Structures

Cassio A O Moraes; Rafaely B C Santos; Marcos F O Cavalcante; Jhefferson S Guilhermi; Muhammad A Ali; Giancarlo V Botteselle; Tiago E A Frizon; Muhammad I A Shah; Luciano M Lião; Adilson Beatriz; Sumbal Saba; Jamal Rafique

doi:10.1021/acsomega.3c05338

Urea Hydrogen Peroxide and Ethyl Lactate, an Eco-Friendly Combo System in the Direct C(sp²)-H Bond Selenylation of Imidazo[2,1- b]thiazole and Related Structures

ACS Omega. 2023 Oct 12;8(42):39535-39545. doi: 10.1021/acsomega.3c05338. eCollection 2023 Oct 24.

Affiliations

¹ Instituto de Química, Universidade Federal do Mato Grosso do Sul, Campo Grande, Mato Grosso do Sul 79074-460, Brazil.
² LABSO, Instituto de Química, Universidade Federal de Goiás-UFG, Goiânia, Goiás 74690-900, Brazil.
³ Institute of Chemistry (ICS), University of Peshawar-UOP, Peshawar, Khyber Pakhtunkhwa 25120, Pakistan.
⁴ Departamento de Química, Universidade Estadual do Centro-Oeste-UNICENTRO, Guarapuava, Paraná 85819110, Brazil.
⁵ Universidade Federal de Santa Catarina-UFSC, Campus Araranguá, Araranguá, Santa Catarina 88905120, Brazil.
⁶ Department of Chemistry, Abdul Wali Khan University, Mardan, Khyber Pakhtunkhwa 23200, Pakistan.

Abstract

Herein, we describe a urea hydrogen peroxide-mediated sustainable protocol for the synthesis of selenylated imidazo[2,1-b]thiazole by using half molar equivalent diorganyl diselenides in ethyl lactate as a greener solvent. The reaction features high yields, easy performance on gram scale, metal-free conditions, as well as applicability to imidazopyridine and imidazopyrimidine.