107097-23-4Relevant academic research and scientific papers
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.
THE PHOTOCHEMISTRY OF 1-ALKENYLBENZOTRIAZOLES METHODOLOGY FOR THE SYNTHESIS OF INDOLES
Wender, Paul A.,Cooper, Christopher B.
, p. 2985 - 2992 (2007/10/02)
The synthesis of 2-substituted, 3-substituted and 2,3-disubstituted indoles based on the photolysis of 1-alkenylbenzotriazoles is described along with the application of this method to the synthesis of the 2,3-dihydropyrroloindole nucleus of the mitomycin antitumor antibiotics.
