246-06-0Relevant articles and documents
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Anderson,Tazuma
, p. 3455 (1952)
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THE REACTION OF 1,4-DIHYDROCYCLOPENTINDOLES WITH DIMETHYL ACETYLENEDICARBOXYLATE
Kurihara, Takushi,Nasu, Keiko,Haginaga, Satomi
, p. 2456 - 2459 (2007/10/02)
Diethyl 1,4-dihydro-4-methyl-3-(N-methyl-3-indolyl)cyclopentoindole-1,2-dicarboxylate (3) reacted with dimethyl acetylenedicarboxylate (DMAD) in acetonitrile under reflux to give the 5,10-dihydrocyclopentindole (5).The same reaction in benzene gave the maleate (or fumarate) (6) and the 1,1a,3a,4-tetrahydrocyclobutcyclopentindole (8).Thermolysis of 8 resulted in the formation of 5.In contrast to a cycloaddition reaction of 3 and DMAD, 2 reacted with two molecules of DMAD to give the 1,1a,5a,6-tetrahydrocyclohexcyclopentindole (10).Keywords: 1,4-dihydrocyclopentindole; dimethyl acetylenedicarboxylate; cycloaddition; 5,10-dihydrocyclopentindole; tetrahydrocyclobutcyclopentindole; tetrahydrocyclohexcyclopentindole.