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16.13.3.1.3 Method 3: Removal of Heterofunctional Groups

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416675.

3-Aminoquinazoline-2,4(1H,3H)-diones 223 (R2=OH) are successfully deaminated with nitrous acid to give quinazoline-2,4(1H,3H)-diones 34 (R2=OH) (Scheme 155).[‌688‌] Deamination of 3-aminoquinazolin-4(3H)-ones 223 (R2=H) can generally be performed in excellent yields with nitrous acid.[‌161‌,‌162‌,‌287‌,‌689‌,‌690‌] Raney nickel in boiling alcohol,[‌161‌,‌162‌] potassium permanganate in boiling acetone,[‌693‌] or lead(IV) acetate in dichloromethane[‌694‌‌697‌] are also sometimes used for deamination of 3-aminoquinazolin-4(3H)-ones. Some additional examples in which aromatization is achieved by removal of N-functional groups are collected in Table 7.[‌698‌‌701‌]

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