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16.13.3.1.1 Method 1: Oxidation of Hydro Precursors

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416670.

Syntheses of 1,2-dihydroquinazolines, 3,4-dihydroquinazolines, and 1,2,3,4-tetrahydroquinazolines, from which quinazolines are obtained by oxidation, are not treated in this article. For some relevant synthetic methods, see various reviews and papers.[‌5‌,‌522‌,‌654‌‌669‌]

8-Meee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eeee eee eeeeeeee ee 8-eeeeeeeeeeeeee-8(8M)-eeee 88 eeee eeeeeeeee eeeeeeeeeeee ee eee eeeeeee (Meeeee 888).[‌888‌,‌888‌] Meeee eeeee eeeeeeeeee eee eeeeee eeeeeee ee 8,8-eeeeeee-8-eeeeeeeeeeeeeeee-8(8M)-eee eeeeeee eeeeee.[‌888‌] 8,8-Meeeeeeeeeeee 8,8-eeeeeeeeeeeeeeeeee 8-eeeeee eee eeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeeeeeee 8-eeeeee 888 ee eeeeeeeee(MM) eeeee ee eeeeeeeeeeeeeee,[‌888‌,‌888‌] eeeeeeeee eeeeeeeeeeee ee eeeeeeeeee,[‌888‌] eeeeeeeee eeeeeeeeeeee ee eeee(MMM) eeeeeeee ee eeeeeee,[‌888‌] ee eeee(MM) eeeeeee[‌888‌] (Meeeee 888).

Meeeee 888 Meeeeeeee ee 8-Meee-8,8-eeeeeeeeeeeeeeeee-8(8M)-eeee ee 8-Meeeeeeeeeeeee-8(8M)-eeee[‌888‌,‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Meeeeeeeeeeee 8,8-Meeeeeeeeeeeeeeeee 8-Meeeee ee 8,8-Meeeeeeeeeeee Meeeeeeeeee 8-Meeeee[‌888‌,‌888‌‌888‌]

Meeeeeeeeee 888

M8 M8 M8 M8 Meeeeee Meeeeeeeee Meeee (%) ee (°M) Mee
Me Me Me Me MMeM8 MMMe8, ee, 8.8e 88 888888 [‌888‌]
MM8Me 8-MM8M8 M M MeM8 MM8Me8, eeeeee, 8e 88 888888 [‌888‌]
MM8Me 8-MM8M8 Me M MeM8 MM8Me8, eeeeee, 8e 88 888888 [‌888‌]
MM8Me 8-MeM8M8 MM8 M MeM8 MM8Me8, ee, 88e 88 888888 [‌888‌]

8,8-Meeeeeeeeeeeeeeeeee eee eeeeee eeeeeeee ee eeeeeeeeeeee 88 ee eeeeee,[‌888‌,‌888‌] 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee[‌888‌,‌888‌,‌888‌] ee eeeeeeeee eeeeeeeeeeee[‌888‌] (Meeeee 888). 8,8-Meeeeeeeeeeeeeeeeee eee eeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeee 88 eeee eeeeeeeee ee eeeeee eeeeeeeeeeee ee eeeeeeee eeeeeee eeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌‌888‌] ee eeee eeeeeeeee(MM) eeeee[‌888‌,‌888‌] ee eeeeeeeeee ee eeeeeee eeeeeeee (Meeeee 888). Meeeeeeee eeeeeeeeeeee ee eeeeee eeee eee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeeeeee eee eeee eeee eeeee.[‌888‌,‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 888

M8 M8 M8 Meeeeee Meeeeeeeee Meeee (%) ee (°M) Mee
Me Me M MMM eeeeeee, 888°M, 8.88e 888 888888 [‌888‌]
Me Me M M8 MeMM, eeeeeeeeeeeeeeeee 888888 [‌888‌]
Me MMe M MMM eeeeeee, eeeeee, 8e 88 8888 [‌888‌]
Me MMe M M8[Me(MM)8] eeeeeee/MeMM, ee, 8e 88 8888 [‌888‌]
MM8M Me M M8 MMM, ee, 88e 88 888 [‌888‌]
MM8M 8-MeM8M8 8-Me M8 MMM, ee, 88e 88 888888 [‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeeeeee 888

M8 M8 Meeeeee Meeeeeeeee Meeeee (%) ee/ee (°M) Mee
M M M8[Me(MM)8] MMM, M8M, ee, 8.8e 88 8888.8 [‌888‌]
Me M Me8[Me(MM)8] MMM, M8M, ee, 8e e.e. 8888 [‌888‌]
Me M Me8[Me(MM)8] MMM, M8M, ee, 8e e.e. 888888 (eeeeeee) [‌888‌]
M Me M8[Me(MM)8] MMM, M8M/eeeeeee, ee, 8e 88 8888 [‌888‌]
M e-Me MMeM8 eeeeeee, ee, 88e 88 88/8.88Meee [‌888‌]
M MM=MM8 M8[Me(MM)8] MMM, M8M, ee, 8e 88 eee [‌888‌]
M Me M8[Me(MM)8] MMM, M8M/eeeeeee, eeeeee, 8.8e 88 88888 [‌888‌]
M 8-eeeeeee M8[Me(MM)8] MMM, M8M, ee, 888e 88 888 [‌888‌]
8-Mee M MeM8 eeeeeee, eeeeee, 8e 88 8888 [‌888‌]

e e.e.=eee eeeeeeee.

Meeeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee ee eee eeeeeeeeeeee 888 ee eeeeeee eeeeeeeeeeee ee eeeeeeeee eeeeeeeeeeee ee eeeeeee/eeeee,[‌888‌] eee ee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee ee eeeeeeeeeeeeeeee-8,8-eeeeeee ee eeeeeee[‌888‌] (Meeeee 888).

Meeeee 888 Meeeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeeeeee ee Meeeeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeee 888

M8 M8 M8 Meeeeee Meeeeee Meee (°M) Meee (e) Meeee (%) ee (°M) Mee
Me M M MMM eeeeeee ee 8 88 eee eeeee [‌888‌]
8-MMM8M8 M M MMMe eeeeeee eeeeee 8 88 888888 [‌888‌]
8-eeeeeee M M MMMe eeeeeee eeeeee 8 88 888888 [‌888‌]
Me Me Me MMeM8 eeeeeee/M8M ee 88 888888 [‌888‌]
8-M8MM8M8 Me M MMeM8 eeeeeee/M8M ee 88 888888 [‌888‌]

e MMM=eeeeeeeeeeeeeeee-8,8-eeeeeee.

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-(eeeeeeeeeeee)-8-(8-eeeeeeeeeeee)eeeeeeeeeee 8-Meeee (888, M8=MM8Me; M8=8-MM8M8; M8=Me; M8=M); Meeeeee Meeeeeeee:[‌888‌]

Me 8-eeeeee-8-(eeeeeeeeeeee)-8-(8-eeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeeeee 8-eeeee (8e, 88.8eeee) ee MM8Me8 (888eM) eee eeeee eeeeeeeee MeM8 (88e, 888.8eeee), eee eee eeeeeeee eee eeeeeee eee eeeeeeee eee 8e. Mee eeeeeee eee eeeeeeee eeeeeee Meeeee, eeeee eee eeee eeeeee eeee MM8Me8/MeMM (8:8; 888eM). Mee eeeeeeee eeeeeeeee eeee eeeeeeeeee eee eee eeeeeee eee eeeeeeeeeeee (MeMM); eeeee: 8e (88%); ee 888888°M (eee-eeeee eeeeee, MM8Me8/eeeeee).

8-Meeeeeeeeeeeeeeee-8-eeeeeeeeee Meee (88, M8=MM8M; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeeee: Me eeeeee-eee eeee ee e 8-eeee-8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee eeee (88eeee) ee MMM (88eM) eee eeee ee eeeeee eeeeeeee eee 8e; eee eeeee ee eee eeee eeeeeee ee eeeee eeeeee. Meeeeeee ee M8M (88eM) eeee e eeeeeeeeeee, eeeee eeeee eeeeeee ee 8°M eee eeeeeeee ee eeeeeeeeee, eeeeeeee ee eeeeeee eeee M8M eee Me8M.

8-Meeeeeeeeeeeeeeee (88, M8=M; M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeee Meeeeeeeeeee Meeeeeeee: 8-Meeeee-8,8-eeeeeeeeeeeeeeeeee (8e, 88eeee) eee eeeeeeeee ee eeeeeee ee ee e eeeeeee ee M8M (888eM) eee eeeeeee (888eM). M eeee ee MMM (88e, 888eeee) ee M8M (88.8eM) eee eeeee eee eee eeeeeee eee eeeeee ee eee eeeee eeee eeeeee eee eeeee eeeeeeee ee e eeee ee M8[Me(MM)8] (88.8e, 88eeee) ee M8M (888eM). Meeeeee eeee eeeeeeeeee eeeeeee eee eeeeeeeee eee 8eee, eee eee eeeeee eeeeeee eee eeee eeeeeee eeee M8M, eeeeeeee eeee ee MeMM, eee eeeeeeeee eeee Me8M. Meeeeee ee eee eeeeeeee, eeeeeee ee eeeeeee eeeeeeee, eeee eee eeeee (Me8MM8) eeeeeee eeee e eeeeee eeee eeeeeee; eeeee: 8.8e (88%); ee 88888°M.

Meeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Meeeeeeeeeeee eeee 8,8-Meeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee ee Meeeeeeeeeeeeeee-8,8-eeeeeee: M eeeeeeeeee ee eee 8,8,8,8-eeeeeeeeeeeeeeeeeeeee (88eeee) eee MMM (8.88e, 88eeee) ee MMM (8.88e, 88eeee) ee eeeeeee (88eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eee 88eee ee ee (eee MMM) ee eeeee eeeeee (eee MMM). Mee eeeee eee eeeeeeee eee eeeeee eeee eeeeeee (88eM). Mee eeeeeeee eee eeeeee eeee 8.8M MeMM (88eM) eee eee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8 (8×88eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeee eee eeeee eeeeeeeeeee.

References


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