General Papers ARKIVOC 2006 (ix) 1-16
(CN) H S (NH)
N
N NN Ph S Ar Ar N N H Ar R1 COOR H R1 Me N N N Me N H COOR HN N
H2NCO
68 6970 Me
Reactions with diethyl(ethoxymethylene)malonate or 3-formylchromone gave pyrimidine derivatives 71 or 72, respectively54.
O
Ar
H Ar
EtOOC
Ar1 EtOOC
COOEt
N
N
Ph NN NNPh
H
H
71 72
Heating the diethanolamine or bis(2-chloroethyl)amine hydrochlorides with aniline derivatives gave 1-arylpiperazine derivatives. The 1-substituted piperazines were deuteromethylated. 1,4-Dithiocarbonyl piperazine was obtained from reaction of benzaldehyde with piperazine and sulfur. 1,4-Diacetylpiperazine-2,5-dione were reacted with aldehydes to give the monoarylidene products and then 73. 4-Benzylpiperazine-2,5-dione was reacted with bromobenzene to give 74. Diels-Alder cycloaddition of pyrazinone with ethene gave 7555,56.
RO O Ph
R
O HNNH Ph
NN
N N Ph
O ArO
Cl
7374 75
Condensation of o-phenylenediamine with methylglyoxal, aldohexoses and aryl or alkyl acyloins gave the corresponding quinoxalines57 76. Indoloquinoxalines were obtained from isatin. Carbethoxymethylation of isatin and then reaction with o-phenylenedimine gave the respective indoloquinoxalines 77, whereas hydrazide was condensed with aromatic aldehydes and monosaccharides. L-Ascorbic acid or D-isoascorbic acid were oxidized with iodine and then reacted with o-phenylenediamine and phenylhydrazine to give quinoxalinones 78, which were cyclized to pyrazolyl-quinazolinones58,59.
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