Intramolecular Cycloaddition of Isomunchnone Dipoles to Heteroaromatic π-Systems was written by Padwa, Albert;Hertzog, Donald L.;Nadler, William R.. And the article was included in Journal of Organic Chemistry in 1994.Name: 3-(1H-Indol-1-yl)propanoic acid This article mentions the following:
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 intramol. 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 intramol. 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. In the experiment, the researchers used many compounds, for example, 3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1Name: 3-(1H-Indol-1-yl)propanoic acid).
3-(1H-Indol-1-yl)propanoic acid (cas: 6639-06-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Name: 3-(1H-Indol-1-yl)propanoic acid
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles