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16.13.4.1.4.4.2 Variation 2: Thioxo Group Transformations

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416704.

Ozonation of 2-thioxo-2,3-dihydroquinazolin-4(1H)-one (23) in acetic acid/water affords quinazoline-2,4(1H,3H)-dione (2) in 75% yield (Scheme 206).[‌789‌] Photolysis of 23 in 1,2-dimethoxyethane or methanol in the presence of electron-poor alkenes produces 2-(sulfanylalkyl)quinazolin-4(3H)-ones (Scheme 207).[‌825‌,‌826‌] Similarly, irradiation of quinazoline-4(3H)-thiones 275 and electron-poor alkenes gives 4-(sulfanylalkyl)quinazolines in high yields.[‌825‌]

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