Reactivity study on morpholine-1-carbothioic acid (2-phenyl-3H-quinazolin-4-ylidene) amide

✍ Scribed by Walid Fathalla; Pavel Pazdera; Michal Čajan; Jaromír Marek

• Book ID: 102339923
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2002
• Tongue: English
• Weight: 110 KB
• Volume: 39
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570390606

✦ Synopsis

Abstract

Regioselective reactions of morpholine‐1‐carbothioic acid (2‐phenyl‐3__H__‐quinazolin‐4‐ylidene) amide (1) with electrophiles and nucleophiles were studied. The compound (1) reacts with alkyl halides in basic medium to afford S‐substituted isothiourea derivatives, with amines to give 1,1‐disubstituted‐3‐(2‐phenyl‐3__H__‐quinazolin‐4‐ylidene) thioureas and l‐substituted‐3‐(2‐phenyl‐quinazolin‐4‐yl) thioureas via transami‐nation reaction. The reaction of (1) with amines in the presence of H~2~O~2~ provided N^4^‐disubstituted‐N'^4^‐(2‐phenylquinazolin‐4‐yl)morpholin‐4‐carboximidamide via oxidative desulfurization. Estimation of reactivity sites on (1) was supported using the ab initio (HF/6‐31G**) quantum chemistry calculations. The ir, ^1^H nmr, ^13^C nmr, mass spectroscopy and x‐ray identified the isolated products.