Cyclohexane-1,2-dione dioxime, reaction

Cyclocondensation of 2-aminobenzoylformic acid 98 and cyclohexane-1,2-dione dioxime 99, followed by decarboxylation with concomitant dehydrogenation of the diacid 100, gave quino[3,2-c]acridine 101 (Scheme 19) (70JPR1105). The same skeleton 102 was obtained from the Ullmann-amine coupling reaction of 2-aminobenzophenone and 1,2-diiodobenzene, followed by ring closure (85LA1501). 

The reaction of hexane-2,5-dione- and cyclohexane-l,4-dione dioximes (representatives of open-chained and cyclic compounds of this series) with acetylene has been studied [272],... 

SCHEME 1.85 Alternative pathways of the reaction between cyclohexane-1,4-dione dioxime and acetylene. 

The dioxime of cyclohexane-1,4-dione reacts with acetylene in an autoclave in the presence of KOH/dimethyl sulfoxide (DMSO) (Trofimov reaction) to give l,5-divinyl-4,8-dihydropyrrolo[2,32f]indole by sequential [1,3]- and [3,3]-rearrangements in poor yield (Equation 91) <2004TL3789>. 

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