Chemistry of halonitroethenes, Part 1: First synthesis of functionalized 3-chloroquinoxalin-2(1H)-one 4-oxides.

[摘要]：Compounds (More Than One Hetero Atom)) Section A 1-pot annulation reaction of aniline and its ring-substituted derivs. with 1,1,2-trichloro-2-nitroethene (TCNiE) was developed delivering 3-chloroquinoxalin-2(1H)-one 4-oxides, exclusively, in good yields. The structure was proved by x-ray anal. of 3-(dodecylthio)-7-methoxyquinoxalin-2(1H)-one 4-oxide [triclinic, space group P1, a 632.32(13), b 900.7(2), c 1935.2(4) pm, a 84.236(19), b 83.827(17), g 77.126(18)? V 1064.9(4)?06 pm3, Z 1]. The C-N cyclization, a competing reaction to the double SNVin reaction of 1,1,2-trichloro-2-nitroethene with amines, can be controlled by the mode of addn. Some of the resulting quinoxalinones are promising candidates with respect to their prospective biol., esp. pharmacol., activity.

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