Search engine for discovering works of Art, research articles, and books related to Art and Culture
Javascript must be enabled to continue!
C-6 Regioselective Bromination of Methyl Indolyl-3-acetate
View through CrossRef
An efficient route to natural occurring methyl 6-bromoindolyl-3-acetate 1c from methyl indolyl-3-acetate 3 was achieved in 3 steps and 68% overall yield. Thus, in order to regioselectively brominate 3 at the C6-position, introduction of electron withdrawing substituents at N1 and C8 was affected to give intermediate 4 in 82% yield. Bromination of 4 with 8 equiv of bromine in CCl4 and washings with aqueous Na2SO3 gave 5 in 86% yield, which was N- and C-decarbomethoxylated by treatment with NaCN in DMSO, affording 1c in 97% yield. The regioselectivity of bromination was evidenced by NMR spectroscopy and X-ray diffraction analysis.
Title: C-6 Regioselective Bromination of Methyl Indolyl-3-acetate
Description:
An efficient route to natural occurring methyl 6-bromoindolyl-3-acetate 1c from methyl indolyl-3-acetate 3 was achieved in 3 steps and 68% overall yield.
Thus, in order to regioselectively brominate 3 at the C6-position, introduction of electron withdrawing substituents at N1 and C8 was affected to give intermediate 4 in 82% yield.
Bromination of 4 with 8 equiv of bromine in CCl4 and washings with aqueous Na2SO3 gave 5 in 86% yield, which was N- and C-decarbomethoxylated by treatment with NaCN in DMSO, affording 1c in 97% yield.
The regioselectivity of bromination was evidenced by NMR spectroscopy and X-ray diffraction analysis.
Related Results
Wohl‐Ziegler Bromination
Wohl‐Ziegler Bromination
Abstract
This reaction is the bromination of unsaturated organic compounds at either allylic or benzylic position (or α‐position of the side chain of other a...
n-Butyl acetate and its isomers – isobutyl acetate and sec-butyl acetate
Determination in workplace air
n-Butyl acetate and its isomers – isobutyl acetate and sec-butyl acetate
Determination in workplace air
n-Butyl acetate and its isomers, isobutyl acetate and sec-butyl acetate, are colorless, flammable liquids with a fruity odour. Because of their physicochemical properties they are ...
Triflic Acid‐Assisted Regioselective Bromination of Quinoxaline Derivatives Enables a Facile Synthesis of Polymer PTQ10
Triflic Acid‐Assisted Regioselective Bromination of Quinoxaline Derivatives Enables a Facile Synthesis of Polymer PTQ10
AbstractPoly[(thiophene)‐alt‐(6,7‐difluoro‐2(2‐hexyldecyloxy)quinoxaline)] (PTQ10) emerges as a promising candidate for donor materials in organic solar cells (OSCs) due to its hig...
Polyvinyl Acetate, Alcohol, and Derivatives, Polystyrene, and Acrylics
Polyvinyl Acetate, Alcohol, and Derivatives, Polystyrene, and Acrylics
AbstractPolyvinyl acetate, the most widely used vinyl ester, is noted for its adhesion to substrates and high cold flow. Polyvinyl acetate serves as the precursor for polyvinyl alc...
Copolymerization Characteristics of Methyl Acrylate and Methyl Methacrylate. II. Analysis of Methyl Acrylate-Methyl Methacrylate Copolymers by Infrared Spectroscopy
Copolymerization Characteristics of Methyl Acrylate and Methyl Methacrylate. II. Analysis of Methyl Acrylate-Methyl Methacrylate Copolymers by Infrared Spectroscopy
Abstract
The infrared absorption spectra of polymers and copolymers of methyl acrylate and methyl methacrylate have been measured, and then used as the basis of a sp...
Factors Affecting the Production of Poly Methyl Galacturonase Enzyme by Sclerotium rolfsii Sacc
Factors Affecting the Production of Poly Methyl Galacturonase Enzyme by Sclerotium rolfsii Sacc
The aim of this work was to investigate the effects of different culture conditions on the production of poly methyl galacturonase enzyme bySclerotium rolfsii and their optimizatio...
Acetate as a metabolic booster for glucose-based bioproduction in Escherichia coli
Acetate as a metabolic booster for glucose-based bioproduction in Escherichia coli
Abstract
Escherichia coli
, a key workhorse in industrial biotechnology, is commonly grown on glucose, which supports rapid gro...
Biological Activities of Lichen-Derived Monoaromatic Compounds
Biological Activities of Lichen-Derived Monoaromatic Compounds
Lichen-derived monoaromatic compounds are bioactive compounds, associated with various pharmacological properties: antioxidant, antifungal, antiviral, cytotoxicity, and enzyme inhi...