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Solid-phase synthesis of 1,3-disubstituted 2-thioxoquinazoline-4-ones using SNAr reaction

✍ Scribed by Shingo Makino; Eiji Nakanishi; Takashi Tsuji

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 88 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00008-9

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✦ Synopsis

We have developed a solid-phase synthesis of diverse 1,3-disubstituted 2-thioxoquinazoline-4-ones. In this synthesis, the fluorine atom on support-bound 2-fluoro-5-nitrobenzoyl amides was substituted with various primary amines, followed by cyclization with thiocarbonyldiimidazole. Since 1-substitutions can be achieved with primary amines, diverse 1,3-disubstituted 2-thioxoquinazoline-4-ones can be efficiently synthesized using this method. Although solid-phase synthesis of 2-thioxoquinazoline-4-ones using 2-methoxycarbonylphenylisothiocyanate has been reported previously, the introduction of 1-substitutions could not be achieved due to the reactivity of the 2-sulfur atom with alkyl or aryl halide.

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