Synthesis of 1‐Acyl‐3,4‐dihydroquinazoline‐2(1H)‐thiones by Cyclization of N‐[2‐(Isothiocyanatomethyl)phenyl] Amides Generated in situ from N‐[2‐(Azidomethyl)phenyl] Amides |
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| Authors: | Kazuhiro Kobayashi Naoki Matsumoto |
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| Affiliation: | Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4‐101 Koyama‐minami, Tottori 680‐8552, Japan, (phone/fax: +81‐857‐315263) |
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| Abstract: | An efficient method for the preparation of 1‐acyl‐3,4‐dihydroquinazoline‐2(1H)‐thiones 5 has been developed. The reaction of N‐2‐(azidomethyl)phenyl] amides 3 , easily prepared by a three‐step sequence starting with (2‐aminophenyl)methanols, with Ph3P, followed by CS2, allowed generation of N‐2‐(isothiocyanatomethyl)phenyl]‐amide intermediates 4 , which underwent cyclization on treatment with NaH to furnish the corresponding desired products in generally good yields. |
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| Keywords: | Quinazoline‐2(1H)‐thiones 3 4‐dihydro‐ Benzyl alcohols 2‐amino‐ Azides Azaphosphoranes Isothiocyanates |
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