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Novel one-pot procedure for the preparation of 3-substituted 2-thioxo-4(3H)-quinazolinones

Abdel-Megeed, Mohamed F., Aly, Youssef L., Saleh, Mohamed A., Abdo, Ibrahim M., El-Hiti, Gamal A. and Smith, Keith 1995. Novel one-pot procedure for the preparation of 3-substituted 2-thioxo-4(3H)-quinazolinones. Sulfur Letters 19 (3) , pp. 129-140.

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Abstract

3-Substituted 2-thioxo-4(3H)-quinazolinones 3 are obtained in reasonable yields by a 'one-pot' procedure involving the reaction of a mixture of an anthranilic acid and a primary amine with carbon disulfide in the presence of potassium hydroxide. This provides a much more convenient approach than methods involving prior formation and isolation of isothiocyanates and is reasonably general. It fails, however, with the weakly nucleophilic 4-nitroaniline which produces benzo-3,l-thiazine-2,4(lH)-dithione 5a instead, via direct reaction between anthranilic acid and carbon disulfide. Other benzo-3,l-thiazine-2,4(lH)-dithiones 5 are obtained in excellent yields by a 'one-pot' procedure involving the reaction of the appropriate anthanilic acid and carbon disulfide in the presence of base. This method is much more convenient than the tedious reaction of phosphorus pentasulfide with isatoic anhydride. 3-Phenyl-2,4-quinazolinedithione 6 could be obtained in a reasonable yield from the reaction of the corresponding thioxoquinazolinone 3a with Lawesson's reagent or from the reaction of benzo-3,l-thiazine-2,4(lH)-dithione 5a with aniline in the presence of base.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
ISSN: 0278-6117
Last Modified: 04 Jun 2017 03:01
URI: http://orca.cf.ac.uk/id/eprint/15626

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