Publication details
Convenient domino synthesis of quinazolin-4(3H)-ylidene carbothioamides and carbamothioates
| Authors | |
|---|---|
| Year of publication | 2017 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1016/j.tet.2017.06.024 |
| Field | Organic chemistry |
| Keywords | imidoyl isothiocyanate; quinazolin-4(3H)-ylidene carbothioamides; quinazolin-4(3H)-ylidene carbamothioate; Cascade reaction; imidoyl chloride; Dimroth rearrangement; intramolecular hydrogen bond. |
| Description | A simple convenient protocol for the synthesis of secondary amine N-(2- (substitutedphenyl)quinazolin-4(3H)-ylidene) carbothioamides and O-alkyl N-2- (substitutedphenyl)quinazolin-4(3H)-ylidene carbamothioates has been described. It involves the cascade reaction of various secondary amines or alcohols with imidoylisothiocyanates in acetonitrile to afford the desired compounds in excellent yields. The reaction time was 48 h under reflux conditions, involved a simple work up, to form 42 examples of pure products in high yields. The precursor imidoyl isothiocyanates were prepared from the corresponding benzanilides and were purified by flash chromatography. |