0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Methyl Group Modification

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416725.

The 2-methyl and 4-methyl groups of quinazolines behave like active methylene groups and react with electrophilic reagents in the presence of a base, forming exocyclic CC bonds.[‌5‌,‌985‌,‌986‌] Thus, butyllithium converts 2-alkylquinazolin-4(3H)-ones 330 into dianions 331 which react with a variety electrophiles, e.g. alkyl halides, deuterium oxide, phenyl isocyanate, and aromatic aldehydes and ketones, to give the corresponding 2-substituted derivatives 332, generally in very good yields (Scheme 247).[‌987‌,‌988‌]

Meeeee 888 Meeeeeee ee Meeeeeeee 8-Meeeeeeeeeeeeee-8(8M)-eeee eeee Meeeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeee ee 8-eeeeeeeeeeeeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee ee e eeee eeeeeeeee eeeeee 8-eeeeeeeeeee eeeeeeeeeeee (Meeeee 888).[‌888‌,‌888‌‌888‌] 8-Meeeeeeeeeeeeeee-8(8M)-eeee 888 (M=MM) eee 8-eeeeeeeeeeeeeeeeee 888 (M=M) eeeeeeee eeee eeeeeeee eeeeeeeee ee eeeeeee, eeeeeeeee eee eeeeeeeeeeeee 8-eeeeeeeeeeeeeee-8(8M)-eeee 888 (M=MM)[‌888‌,‌888‌,‌888‌,‌888‌] eee 8-eeeeeeeeeeeeeeeee 888 (M=M) (Meeeee 888).[‌888‌‌888‌] 8,8-Meeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeee ee eeeeeeee eeeeeee ee 8-eeeeee-8[8-(8-eeeeee-8-eeeeeeeeeeee)eeeeeee]eeeeeeeeeee.[‌888‌] 8-Meeeeeeeeeeeeeee-8(8M)-eee (888, M8=M; M=MM) eeee eeeeeeeee eeeeeeeeeeee ee eee eeeeee eeeee eeee eeeeeeeeeeeeeeeeeeeee,[‌888‌] eeeeeeee eeeeeeeee,[‌888‌] eee eeeeeeee eeeeeeeee.[‌888‌] 8-Meeeeeeeeeeeeeeeee 888 eeeeeeeee eeeeeeee eeee eeeeeeee eeeeeeeee, eeeeee 8-eeeeee eeeeeeeeeee 888,[‌888‌,‌888‌] eeee eeeee eeeeeeeee ee eeee 8-eeeeee-8-[eeeeeeeeee-8(8M)-eeeeeee]eeeeeeeee,[‌888‌,‌888‌] eee eeee M-eeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeee eeeeeeeeeee ee eeee 8-eeeeee-8-[8-eeeeee-8-(eeeeeeeeeee)eeeee]eeeeeeeeeee.[‌888‌] Meeeeeeeeee, 8-eeeeeeeeeeeeeeeee eeeeeeeeeee eeeeeeee eeee 8-(eeeeeeeeeeeee)eeeeeeeeeeee, eeeeeeee 8-[8-(eeeeeeeeeeeee)eeeeee]eeeeeeeeeee eeeeeeeeeee.[‌8888‌,‌8888‌]

Meeeee 888 Meeeeeee ee 8-Meeeeeeeeeeeeeeee eeee Meeeeeeeeeeee[‌888‌,‌888‌‌888‌]

Meeeee 888 Meeeeeeeeeee ee 8-Meeeee- eee 8-Meeeeeeeeeeeeeeeee eeee Meeeeeeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 888

Meeeeee Meee M8 M8 M Meeeeeeeee Meeee (%) ee (°M) Mee
888 M 8-MeMM8M8 MM 888°M, 8e 88 888888 [‌888‌]
888 M 8,8-(MeM)8M8M8 MM 888°M, 8.8e 88 888888 [‌888‌]
888 8-Me 8-eeeeeee MM MeMM, eeeeee, 88e 88 888888 [‌888‌]
888 M Me M MMMe, MeMM, eeeeee, 8e 8 888 [‌888‌]
888 8-Me 8-MeM8M8 MMe8 MeMMe, Me8M, 888°M, 8e 88 888888 [‌888‌]
888 M 8-M8MM8M8 M MeMM, eeeeee 8 888 [‌888‌]
888 M 8-Me8MM8M8 M MeMe8, 888°M, 88e 88 888 [‌888‌]

Mee 8-eeeeee eeeee ee 8,8-eeeeeeeeeeeeeeeeeeee ee eeee eeeeeeee eeeeee eeeeeeeeeee eee Meeeeee eeeeeeee eeee eee 8-eeeeee eeeee. Meee, eeeeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeee eeee eeeee eeeeeee ee eee eeeeeeee ee ee eeeeee eeeee ee eeeeee eeeeeee eeeeeeee eeeeeeeeeeeeeeee ee eeee 8-eeeeeeeeeeeeeeeee-8-eeeeeeeeeeee eeeee (Meeeee 888),[‌888‌] eee Meeeeee eeeeeeee ee 8-eeeeeeeeeeeeeeeeee eeeeeee 8-(eeeeeeeeee-8-ee)eeeee-8-eeeeee (Meeeee 888).[‌888‌,‌8888‌]

Meeeee 888 Meeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeee[‌888‌]

Meeeee 888 Meeeeee Meeeeeee ee 8-Meeeeeeeeeeeeeeeee[‌888‌,‌8888‌]

Me 8,8-eeeeeeeeeeeeeeeeeeee, eee eeeeee eeeee ee eeeeeeee 8 ee eeee eeeeeeee eeeeeeee ee eee 8-eeeeee eeeee eee eeeeeee eeeeeeeeeee eeee M-eeeeeeeeeeeeeeee ee 8,8-eeeeeee-8,8-eeeeeeeeeeeeeeeee (MMM) eeeee eeeeeeeee eeeeeeee ee e eeeeeeee (Meeeee 888).[‌888‌,‌888‌,‌888‌]

Meeeee 888 Meeeeee Meeeeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeee eee eeeeeeeee ee 8-(eeeeeeeeeeee)eeeeeeeeeee 8-eeeeee 888 eeee eeee ee eeeee eeeeeee eeeeee,[‌888‌,‌888‌] eeeeeeeee eeeeee,[‌888‌,‌888‌,‌8888‌‌8888‌] eeeeeeeeeeeee,[‌8888‌] eeeeeeeee,[‌888‌] eeeeeeeeeee,[‌888‌] eeeeeee,[‌888‌] eee eee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeeee[‌888‌] eeeeee eee eeeeeeeeeeee eeeeeeee 888 (Meeeee 888), eee eeeeeeee ee 888 eeee eeeeeee eee eeeee eeeeeee eeeeee,[‌888‌,‌888‌,‌888‌,‌8888‌‌8888‌] eeeeee eeeeeeeeee,[‌888‌,‌888‌] eee e eeeeeee ee eeeeeeeeee eeeeeee eeeeeeeeee,[‌888‌,‌8888‌,‌8888‌] ee eee eeeeeeee, eeeee ee eeee-eeeeeeeee eeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeeee. Meee ee e eee eeeeeeeeeee eeeee ee eee eeeeeeeee ee 8-(eeeeeeeeeeee)eeeeeeeeeee 8-eeeeee eeee eeeeeeeeeee eeeeee eee eeeeeeeeeeee 8-[(eeeeeeeeeee)eeeeee]eeeeeeeeeee 8-eeeee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeee ee 8-(Meeeeeeeeeee)eeeeeeeeeee 8-Meeeee eeee Meeeeeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeee Meeeeeeeee-8(8M)-eeee 888 (M8=M); Meeeeee Meeeeeeee:[‌888‌]

M 8.8M eeee ee MeMe (8.88eM, 8.8eeee) eee eeeee eeeeeeee ee e eeeeeee eeee ee 8-eeeeeeeeeeeeeeee-8(8M)-eee (8.88e, 8.8eeee) ee eeeee MMM (88eM) eeeeeeeeee ee 88°M eeeee M8. Meeeeeeee ee eee eeeeeee eee eeeeeeee ee e eeee eeee eee eeee. Mee eeeeeee eee eeeeeee ee 88°M eee ee eeeeeeeeee 8e, eeeee eeeee eeee ee eeeeeeeeeeee (8.8eeee) ee MMM (8eM), ee eeeee, eeeeeeeee eeee, eee eeeee. Mee eeeeeee eee eeeeeee eee 8e, eeee eeeeeee eeee eee eeeeeee eeee eee eeeeeee ee eeee ee ee, eeeeeee eeee MeMMe (88eM), eee eeeeeeee eeee ee eee. MM8Me eeee (88eM). Mee eeeeeee eeeee eee eeeeee eeee M8M (8×88eM), eeeee (MeMM8), eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eeee eeeeeeeeeeeeee (MeMM).