Using a Keto Amide, Nitrile, Acyl Halide, or Related Synthon

Using a Keto Amide, Nitrile, Acyl Halide, or Related Synthon [Pg.34]

Keto amides (or thioamides) could participate in cyclocondensations by elimination of the amino or oxo (thioxo) function from the amide (thioamide) grouping according to conditions. The other synthons should behave reasonably predictably. The following examples illustrate some possibilities. [Pg.34]

2-Benzenediamine (233) and C-benzoyl-A -phenyl(thioformamide) (234) gave 2-anilino-3-phenylquinoxaline (235) (pyridime, reflux, 10 h 81%) or 3-phenyl-2(l//)-quinoxalinethione (236) (MeOH-AcOH, 20°C, N2, 3 days 46%) several analogs were made similarly. [Pg.34]

The same substrate (233) and A-benzenesulfonyl-C-benzoylformamide (237) gave only 3-phenyl-2(l//)-quinoxalinone (238) (MeOH, reflux, 15 min 57% Me0H-H20, reflux, 1 h 46% neat reactants, 90°C, 5 min 41%). [Pg.34]

2-Benzenediamine (239) and the bisbisulfite complex (240) (isolated from isonitrosoacetone and an excess of aqueous NaHSOa) gave 3-methyl-2-quinoxalinamine (241) (no details 10%) [Pg.34]

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