Work

Efficient Solid-Phase Synthesis of 3-Substituted-5-Oxo-5H-Thiazolo[2,3-b]-Quinazoline-8-Carboxamides under Mild Conditions with Two Diversity Positions

Year: 2007

Type: article

Abstract: Highly efficient solid-phase synthesis of thiazolo[2,3,b]quinazolines under mild conditions was developed using resin-bound 2-amino-terephthalamic acid, Fmoc-NCS, and bromoketones. Primary amines immobilized to an acid-cleavable backbone amide linker were acylated with 1-methyl-2-aminoterephtalate. Following cleavage of the methyl ester, Fmoc-NCS was used to form a resin-bound thiourea. Bromoketones were subsequently added to form an aminothiazole ring and the cyclization was performed using DIC/HOBt to afford thiazolo[2,3,b]quinazolines. Highly efficient solid-phase synthesis is amenable to high throughput/combinatorial synthesis.

Source: Journal of Combinatorial Chemistry

DOI: 10.1021/cc700122a

Authors: Isabelle Bouillon, Viktor Krchňák

Institution: University of Notre Dame

Language: English

Topic: Quinazolinone synthesis and applications

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1242290637, Diversity oriented combinational synthesis of bisheterocyclic libraries