Yamazaki, Kazuo; Nakamura, Yosuke; Kondo, Yoshinori published an article about the compound: Methyl 5-methoxyindole-2-carboxylate( cas:67929-86-6,SMILESS:O=C(C(N1)=CC2=C1C=CC(OC)=C2)OC ).Application of 67929-86-6. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:67929-86-6) through the article.
Indolecarboxylates are prepared on solid support using palladium-catalyzed reactions as the key steps. Supported β-amino-α,β-unsaturated esters are prepared either by attachment of tert-Bu acetoacetate to a resin followed by condensation with 2-haloanilines or by condensation of acryloyl chloride with a resin followed by Wacker-type oxidation of 2-haloanilines with the resin-bound acrylate in the presence of palladium catalysts. Supported α-amino-α,β-unsaturated esters are prepared by coupling of diethylphosphonoacetic acid to a resin followed by diazo transfer, rhodium-catalyzed insertion of 2-haloanilines, and base-mediated olefination with aldehydes. Palladium-catalyzed cyclization reactions of the α- or β-amino-α,β-unsaturated esters followed by cleavage of the resin-bound esters with sodium methoxide yields indolecarboxylates in moderate yields and purities. Rhodium-catalyzed insertion reactions of aminophenyl ketones and aldehydes with α-diazophosphonate esters followed by base-mediated cyclocondensation and cleavage from the resin with sodium methoxide also yields indolecarboxylates in low to moderate yields and purities. Resin-bound β-(halophenyl)-α-aminoacrylates are prepared either by attachment of an aminoacrylate to a resin followed by Heck arylation with an aryl halide or by rhodium-catalyzed insertion of an amine into a resin-bound α-diazophosphonate followed by olefination with halobenzaldehydes. Palladium-catalyzed cyclization of the resin-bound β-(halophenyl)-α-aminoacrylates followed by resin cleavage yields indolecarboxylates in 43-98% yields. A shorter version of this synthesis is also employed; palladium-catalyzed Heck reaction of 1,2-dihaloarenes with resin-bound acetylaminoacrylic acid followed by resin cleavage yields indolecarboxylates directly in 31-99% yields. Formylbromoarenes and -heteroarenes and methoxycarbonylarenes and -heteroarenes such as Me 2-bromobenzoate undergo palladium-catalyzed coupling with resin-bound acetylaminoacrylic acid followed by cyclization to yield fused pyridines and pyridones such as Me 1,2-dihydro-1-oxo-3-isoquinolinecarboxylate in 52-62% yields.
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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem