You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.16.13.4.4.1 O/S-Functional Group Modification
Please login or sign up for a free trial to access the full content.
Kikelj, D., Science of Synthesis, (2004) 16, 722.
The reaction of quinazoline-2,4(1H,3H)-dione (2) with chlorotrimethylsilane[919] or hexamethyldisilazane[921] affords 2,4-bis(trimethylsiloxy)quinazoline in high yield (Scheme 239). Although alkylation of quinazolin-4(3H)-ones (321, X = O) generally occurs at N3 (see Section 16.13.4.2.2.2) with the Claisen method,[965] using alkyl or aryl halides or dialkyl sulfate[801] and potassium carbonate in acetone or butanone, alkylation of quinazolin-4(3H)-ones produces the O-alkyl derivatives 322 (X = O) in good yields (Scheme 240).[683,793,800,801,966] Selective O-alkylation also takes place when a C2 substituent prevents alkylation at N3 through steric and/or electronic effects.[332,800] Methylation of quinazolin-4(3H)-one with diazomethane affords 4-methoxyquinazoline in 20% yield.[822] Alkylation of quinazoline-4(3H)-thiones 321 (X = S) with alkyl halides[811–813,843,910,967] or dialkyl sulfates[814,815] usually takes place on the sulfur atom, giving the 4-(alkylsulfanyl) derivatives 322 (X = S) (Scheme 240). Similarly, quinazolin-4(3H)-ones react with Merrifield resin in dimethylformamide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene to give the resin-supported quinazolines in excellent yields.[845]
Meeeee 888 Meeeeeeeeeeeeeeeeee ee Meeeeeeeeee-8,8(8M,8M)-eeeee[888,888]
Meeeee 888 M- eee M-Meeeeeeeee ee Meeeeeeeee-8(8M)-eeee eee Meeeeeeeeee-8(8M)-eeeeeee[888,888,888,888,888,888,888,888,888,888,888]
| M8 | M8 | M8 | M | M | Meee | Meeeeee | Meee (°M) | Meee (e) | Meeee (%) | ee (°M) | Mee |
|---|---|---|---|---|---|---|---|---|---|---|---|
| M | M | MM(Me)MM8Me | M | Me | M8MM8 | eeeeeeee | eeeeee | 8 | 88 | 88–88 | [888] |
| M | Me | MM8MM8Me | M | Me | M8MM8 | eeeeeee | eeeeee | 88 | 88 | 888 | [888] |
| M | MM8 | (MM8)8MM=MM8 | M | Me | M8MM8 | eeeeeee | eeeeee | 88 | 88 | 88.8 | [888] |
| M | eeeeeeeeee | (MM8)8Me | M | M | MeM | MMM | 88 | 8.8 | 88 | 888–888 | [888] |
| M | MM8Me | MM(Me)MM8Me | M | Me | MeM | MMMM | ee | 8 | 88 | 88–88 | [888] |
| M | M | Me | M | M | MeMM | M8M | 88 | 8 | 88 | 88–88 | [888] |
| M | M | Me | M | Me | MMMe | eeeeeeeeeee/M8M | eeeeee | 88 | 88 | eee | [888] |
| M | Me | eeeee | M | Me | Me8M | eeeeeee | eeeeee | 8 | 88 | 88 | [888] |
| M | Me | MM8Me | M | Me | Me8M | MeMM | eeeeee | 8 | 88 | 888 | [888] |
| 8-Me | MM8 | Me | M | M | MeMM | M8M | ee | 8.8 | 88 | 888.8 | [888] |
e MMMMM eeee ee e eeeeeeee.
Me 8-eeeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee (88), eeeeeeeeee eee eeeeeeeee eeeee eeeee ee eee eeeeee eeee ee eeee 8-(eeeeeeeeeeeee)- eee 8-(eeeeeeeeeeee)eeeeeeeeee-8(8M)-eeee 888 (Meeeee 888).[888,888–888] Meeeeeeeeee-8,8(8M,8M)-eeeeeeee (88) ee eeeeeeeeee ee 8,8-eee(eeeeeeeeeeeeee)eeeeeeeeeee (888) eeee eeeeeeeeeee ee eeeeeee eeeeee eeeeeeeee,[888,888] eeeeeee eeee ee eeeeee ee eeeee eeeeeeeeeee–eeeeeeee eeeee eeeeeee ee eee eeeeeeeeeeee e eeeeeeeeeeeeee eeeeeeeeeee ee 8-(eeeeeeeeeeeeee)eeeeeeeeeee-8(8M)-eeeeee (888) eeeee eeeee (Meeeee 888).[888] Me(eeeeeeeeee-8-ee) eeeeeeeeee eee eeeeeeee ee eeeeeeeee ee eeeeeeeeeee-8(8M)-eeeeeee eeee eeeeee eeeeeeee eee eeeee eeeeeeee ee eee eeeeeeeeeeee ee eeee eeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeee eee Meeeeeeee ee 8-Meeeee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eee[888,888–888]
Meeeee 888 Meeeeeeeeee ee Meeeeeeeeee-8,8(8M,8M)-eeeeeeee[888,888]
Meeeee 888 Me(eeeeeeeeee-8-ee) Meeeeeeeee eeee Meeeeeeeeee-8(8M)-eeeeeee[888]
Meeeeeeeeeee 888 eeeeeee e eeeeeee eeeeeeeeeee ee eee eeeeeee eeee, eeeee eee eeeeeee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeee eeeeeeeeee (eee Meeeeee 88.88.8.8), eee eeeeeeeeeeee ee eeeeeeeeeeeeeeeeeee 888 eeee eeeeeeeeeee[888,888,888] ee eeeeeeeee eeee,[888] eeeeeeee eeeeeeeeeee,[888,888,888] eeeee eeeeeeeeee,[888,888,888] eeeeee eeeeeeeeeeeeeee,[888] ee eeeeeeeeee eeeeeeeeeeeee[888] (Meeeee 888). Mee eeeeeeeee eeeee ee 8-eeeeeeeeeeeeeeeeeee-8-ee 8-eeeee ee eeeeeeeeeeeeee eeeeeee eeee eee M-eeeee eeeee ee eeeeeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeeeeeee eeee Meeeeeeeeeeeeeeeeee[888,888,888,888]
| Meeeeeee ee MMe/MM | M8 | M8 | M8 | Meeeeee | Meeeeeee Meeeeeeeee | Meeee (%) | ee °M) | Mee |
|---|---|---|---|---|---|---|---|---|
| 8 | M | MM | M | MMe8 | MM8Me8, eeeeee, 8 e | 88 | >888 | [888] |
| 8 | MM=MMMe | MM | M | MMe | MeMM, M8M, eeeeee, 88 e | 88 | 888–888 | [888] |
| 8,8 | M | MM | 8-Me | MMe8 | eeeeeee, eeeeee, 8 e | 88 | eee | [888] |
| 8,8 | M | 8-MeM8M8MM | M | ee•MMe | 888°M, 8 e | e.e.e | >888 | [888] |
e e.e. = eee eeeeeeee.
Meeeee 888 Meeeeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeeee-8-ee 8-Meeee[888]
References
| [111] | Meeeeeee, M. M.M., M. Meee. Mee., (8888), 888. |
| [178] | Meeeeee, M.; Meeeeeee, M., Meeee. Meeeee., (8888) 88, 88. |
| [303] | Meeeee, M.; Meeeeee, M., M. Meee. Mee., (8888), 888. |
| [326] | Meeeee, M. M.; Meeee, M. M., Meeeeeeeeeee, (8888) 88, 8888. |
| [332] | Müeee, M.; Meeee, M.; Meeee, M., Meee. Meee. Meee, (8888) 88, 8888. |
| [403] | Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [493] | Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [683] | Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [783] | Meeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 8, 888. |
| [793] | Meeöeeeeee, M.; Meeeee, M., M. Meeeeeeeeee., M, (8888) 88, 888. |
| [800] | Meee, M.; Meeeee, M.; Meee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
| [801] | Meeeee, M., Mee. Meee. Meee., (8888) 88, 888. |
| [811] | Mee, M. M.; Meeeeee, M. M.; Meeeee, M. M., M. Meee. Mee., (8888), 8888. |
| [812] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeee, M.; M'Meeeee, M. M.; Meeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [813] | Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [814] | Meee, M. M., M. Meee. Mee., (8888), 8888. |
| [815] | Meeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [822] | Meeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [843] | Meee, M.; Meeeee, M., Meeeee Meeeeee Mee. Meee., (8888), 8888. |
| [845] | Meeeeeeee, M. M.; Meee Me-Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [867] | Meeeeeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meee, M.; Meee, M. M.; MeMeeeeee, M.; Mee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [910] | Meeeee, M.; Meeeee, M.; Meeeeee, M. M., Meeeeee Mee. Meee., (8888), 888. |
| [919] | Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [921] | Meeeeeeeee, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 888. |
| [933] | Mee, M. M.; Mee, M. M., Meee. Meeee. (Meeeeeee, Mee.), (8888) 888, 888. |
| [941] | Meeee, M.; Meee, M.; Meeee, M., M. Meee. Mee., Meeeeeeee, (8888), 888. |
| [965] | Meeeeee, M.; Meeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 88. |
| [966] | Meeee, M. M.; Meeeeee, M.; Meeee, M. M., Meeeee M. Meee., Meee. M, (8888) 88, 88. |
| [967] | Meeeš, M.; Mežeee, M.; Meee, M.; Meeeeee, M.; Šeeeáeee, M.; Meeeee, M., Meeeeee, (8888) 88, 888. |
| [968] | Mee, M. M.; Meeeeeeee, M.; Meeeeeeeeeeee, M. M.; Meeeeeeee, M. M.; M'eeeee, M. M., Meee. Meeeeeeeeee. Meeeee., (8888), 888; Meee. Meeee., (8888) 888, 888888. |
| [969] | Mee, M. M.; Meeeeeeee, M.; Meeeeeeee, M. M.; M'eeeee, M. M.; Meeeeeeeeeeee, M. M., Meee. Meeeeeeeeee. Meeeee., (8888), 8888; Meee. Meeee., (8888) 888, 888888. |
| [970] | Meeeeee, M.; Müeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
| [971] | Meeeeee-Meéeee, M.; Meeeeee, M., Meee Meee. Meee., (8888) 888, 888. |
| [972] | Meeee, M. M.; Mee, M. M.; Mee, M. M.; Me, M. M.; Meeee, M. M.; Mee, M. M.; Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [973] | Meeeeee-Meéeee, M.; Meeeeee, M.; Møeeee, M., Meee Meee. Meee., (8888) 888, 88. |
| [974] | Meeeeeeee, M. M., Me Meeeee–Meee, (8888); Mee. MM/8e, e 888. |
| [975] | Meeeeeeee, M. M., Me Meeeee–Meee, (8888); Mee. MM/8e, e 888. |
| [976] | Mee, M. M.; Meeee, M. M.; Meeeeee, M.; Meeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8, 8888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 8e8, 888.
Return to Top