Heaner, William L. IV’s team published research in RSC Advances in 3 | CAS: 20538-12-9

RSC Advances published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Related Products of indole-building-block.

Heaner, William L. IV published the artcileIndoles via Knoevenagel-Hemetsberger reaction sequence, Related Products of indole-building-block, the publication is RSC Advances (2013), 3(32), 13232-13242, database is CAplus.

A series of substituted indoles was designed and the synthesis of the target compounds was achieved by a sequential reaction of aromatic aldehyde with Et (azido)acetate in the presence of sodium ethoxide to form a corresponding Et α-(azido)-β-(aryl)acrylate (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the Et α-azido-β-(aryl)acrylates were significantly increased when employing sacrificial electrophile Et trifluoroacetate. 1H NMR and coupled 1H-13C NMR anal. of the Et α-azido-β-arylacrylates indicate that the condensation is stereospecific-only the (Z)-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted Et α-azido-β-arylacrylates resulted in the formation of both the 5-substituted indole derivatives and 7-substituted indole derivatives (the 5-regioisomer being slightly favored over the 7-regioisomer). Analogous thermal treatment of di-Et (2Z,2Z’)-3,3′-(1,3-phenylene)bis[2-(azido)acrylate] and di-Et (2Z,2Z’)-3,3′-(1,4-phenylene)bis[2-(azido)acrylate] exclusively produced pyrroloindole derivatives, di-Et 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and di-Et 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, resp. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification

RSC Advances published new progress about 20538-12-9. 20538-12-9 belongs to indole-building-block, auxiliary class Indole,Ester,Ether, name is Ethyl 7-methoxy-1H-indole-2-carboxylate, and the molecular formula is C12H13NO3, Related Products of indole-building-block.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles