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Two-Step Synthesis of 1,3-Disubstituted 3,4-Dihydro-4-thioxoquinazolin-2(1H)-ones from 1-Bromo-2-fluorobenzenes

✍ Scribed by Kazuhiro Kobayashi; Toshihide Komatsu; Yuki Yokoi; Hisatoshi Konishi

Publisher
John Wiley and Sons
Year
2011
Tongue
German
Weight
141 KB
Volume
94
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

An efficient synthesis of 3‐alkyl‐3,4‐dihydro‐4‐thioxobenzoquinazolin‐2(1__H__)‐ones 3 has been accomplished in two steps and in satisfactory yields from 1‐bromo‐2‐fluorobenzenes 1. Thus, the reaction of 1‐fluoro‐2‐lithiobenzenes, generated by the Br/Li exchange between 1 and BuLi, with alkyl isothiocyanates, gives N‐alkyl‐2‐fluorobenzothioamides 2, which, in turn, react with a series of isocyanates in the presence of NaH to give the desired products 3.

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ChemInform Abstract: Two-Step Synthesis
ChemInform Abstract: Two-Step Synthesis of 1,3-Disubstituted 3,4-dihydro-4-thioxoquinazolin-2(1H)-ones from 1-Bromo-2-fluorobenzenes.
✍ Kazuhiro Kobayashi; Toshihide Komatsu; Yuki Yokoi; Hisatoshi Konishi 📂 Article 📅 2011 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

Two-Step Synthesis of 1,3-Disubstituted 3,4-dihydro-4-thioxoquinazolin--2(1H)-ones from 1-Bromo-2-fluorobenzenes. -Benzothioamides (III) undergo addition-substitution with phenyl isocyanate (IV) to give the desired thioxoquinazolinones (Va)-(Vc) in good yields. No reaction is observed for (IIId) irr

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