29873-09-4Relevant articles and documents
1, 2, 3, 9-tetrahydro-4H-carbazol-4-one and 8, 9-dihydropyrido- [1, 2-a]indol-6(7H)-one from 1H-indole-2-butanoic acid
Bunce, Richard A.,Nammalwar, Baskar
experimental part, p. 172 - 177 (2009/07/17)
Efficient syntheses of the title ring systems have been developed from 1H-indole-2-butanoic acid, which was easily prepared from 2-fluoro-1- nitrobenzene in four steps. Heating 1H-indole-2-butanoic acid in toluene containing p-toluenesulfonic acid at 110°
Intramolecular Cycloaddition of Isomuenchnone Dipoles to Heteroaromatic ?-Systems
Padwa, Albert,Hertzog, Donald L.,Nadler, William R.
, p. 7072 - 7084 (2007/10/02)
A series of furanyl-, thienyl-, and indolo-substituted diazo imides were prepared by treating the appropriate amides with diketene to give the N-acetoacylated imides.Exposure of the imides to standard diazo transfer conditions afforded the desired diazo imides.Treatment of these diazo imides bearing tethered heterocyclic rings with rhodium(II) acetate affords transient isomuenchnone dipoles.The mesoionic dipoles are formed by cyclization of the rhodium carbenoid onto the neighboring amide carbonyl oxygen atom.The scope and limitations of the intramolecular 1,3-dipolar cycloaddition of the isomuenchnones across a tethered furan and thiophene ring were studied.The facility of the internal cycloaddition is influenced by the length and nature of the tether connecting the dipole and dipolarophile functionalities.The reaction is critically dependent on conformational factors in the transition state.In addition, the first examples of intramolecular cycloaddition of isomuenchnones to indole dipolarophiles are reported.Cycloadditions of this type generate highly functionalized polyheterocyclic systems with complete relative stereocontrol at the newly formed stereocenters.