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Kikelj, D., Science of Synthesis, (2004) 16, 675.
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[694–697] 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.[698–701]
Meeeee 888 Meeeeeeeeee ee 8-Meeeeeeeeeeeeeee-8,8(8M,8M)-eeeeee eee 8-Meeeeeeeeeeeeee-8(8M)-eeee[888,888,888,888–888,888–888]
M8 | M8 | Meeeeee | Meeeeeeeee | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|---|
M | MMe | MeMM8, MeMM | M8M, ee, 88 eee | 88 | >888 | [888] |
8-Me | MMe | MeMM8, MeMM | M8M, ee, 88 eee | 88 | >888 | [888] |
M | MM8 | MeMM8, M8MM8 | <8°M ee ee, 8.88 e | 88 | 888–888 | [888] |
8-Me | 8-MeeMM | Meeee Me | MeMM, eeeeee, 8 e | 88 | 888–888 | [888,888] |
8,8-Me8 | Me | MeMM8, MMe | M8M, 8–8°M | 88 | 888 | [888] |
M | eeeeee-8-ee | MeMM8, MMe | M8M, 8°M, 8 e | 88 | 888–888 | [888] |
M | MM(e-Me)Me | Me(MMe)8 | MMM, MM8Me8, −88°M, 8.8 e | 88 | 888–888 | [888] |
M | Me | MMeM8 | eeeeeee, eeeeee, 8 e | 88 | 888 | [888] |
e Meeeeee ee eeeeeee eeeeeeee eee eeeeeeeeeee.
Meeee 8 Meeeeeeeeeee eee Meeeeeeeee-8(8M)-eeee ee M-Meeeeeeeee Meeee Meeeeee[888–888]
Meeee | Meeeeeee Meeeeeeeee | Meeeeee | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|
MeMM, eeeeee, 88 e | 88 | 888–888 | [888] | ||
eeeeeeeeeee ee 888°M | 88 | 888–888 | [888] | ||
eeeeeeeee eeeee eee ee, 88 eee | e.e.e | e.e.e | [888] | ||
8. MMM, MMM, 88°M 8. MMMMe, 8–88°M 8. ee MM8Me |
88 | 888–888 | [888] |
e MMMM = eeeeeeeeeeeeeeeeeeeeeeeeeeeeee.
e e.e. = eee eeeeeeee.
Meeeeeeeeeee Meeeeeeee
8-(Meeeee-8-ee)eeeeeeeeee-8(8M)-eee (88, M8 = M; M8 = eeeeee-8-ee); Meeeeee Meeeeeeee:[888]
Me ee eee-eeee eeeeeee ee 8-eeeee-8-(eeeeee-8-ee)eeeeeeeeee-8(8M)-eee (8.88 e, 8.8 eeee) eee eeeee MMe (8 eM) eee eeeee MeMM8 (8.88 e, 8.88 eeee) eeeeeeeee ee eeee M8M (8 eM). Meeee eee eeeeeeeee ee M8 eee eeeeee, eee eeeeeee eee eeeeeee eeee M8M (88 eM) eee eee eeeeeee ee eeeee eee 8 e. Meeeeeeee eeeeeeeeee, eee eeeeeeeee eeeeeee eee eeeeee eeeeeeeeee eeee 88% ee MeMMM8; eeeee: 8.88 e (88%); ee 888–888°M.
References
[161] | Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[162] | Meeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M., M. Meee. Mee., Meeeeeeee, (8888), 8888. |
[287] | Meeeee-Meee, M.; Meeeeeeee, M. M.; Meeeeeeeeeee, M. M., Meeeeeeee, (8888), 88. |
[688] | Meeeeeee, M.; Meeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8. |
[689] | Meeeeee, M. M.; Me-Meeeee, M. M.; Me-Meeee, M. M.; Meeee, M. M., Meeeeeeee, (8888) 88, 888. |
[690] | Meeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M.; Meeeee, M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[693] | Meee, M. M.; Mee, M.; Meeeeee, M.; Meeee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 888. |
[694] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888) 888. |
[695] | Meeeeeee, M. M.; Meeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[696] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[697] | Meeeeeee, M. M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[698] | Meee, M. M.; Meeeeee, M. M. M.; Meeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[699] | Meeeeeeee, M. M.; Meee, M. M.; Meeeeee, M., M. Meee. Mee. M, (8888), 8888. |
[700] | Meeeee, M.; Meeeee, M.; Meeee, M., Meeeeeeee, (8888), 888. |
[701] | Meeee, M.; Me-Meee, M. M.; Meeee-Meeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 88.