AUTHOR=Yasaei Zahra , Mohammadpour Zeinab , Shiri Morteza , Tanbakouchian Zahra , Fazelzadeh Shima 

TITLE=Isocyanide Reactions Toward the Synthesis of 3-(Oxazol-5-yl)Quinoline-2-Carboxamides and 5-(2-Tosylquinolin-3-yl)Oxazole

JOURNAL=Frontiers in Chemistry

VOLUME=7

YEAR=2019

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2019.00433

DOI=10.3389/fchem.2019.00433

ISSN=2296-2646

ABSTRACT=<p>A palladium-catalyzed three-component reaction between 5-(2-chloroquinolin-3-yl) oxazoles, isocyanides, and water to yield 3-(oxazol-5-yl)quinoline-2-carboxamides is described. Interestingly, sulfonylation occurred when the same reaction was performed with toluenesulfonylmethyl isocyanide (TosMIC) as an isocyanide source. The reaction with 5-(2-chloroquinolin-3-yl)oxazoles and TosMIC in the presence of Cs<sub>2</sub>CO<sub>3</sub> in DMSO afforded 5-(2-Tosylquinolin-3-yl)oxazoles. In basic media, TosMIC probably decomposed to generate Ts<sup>−</sup> species, which were replaced with Cl<sup>−</sup>. Tandem oxazole formation with subsequent sulfonylation of 2-chloroquinoline-3-carbaldehydes to form directly 5-(2-tosylquinolin-3-yl)oxazoles was also investigated.</p>