33723-33-0

Usage

InChI:InChI=1/C17H16N2O3/c1-22-13-8-6-12(7-9-13)16(11-19(20)21)15-10-18-17-5-3-2-4-14(15)17/h2-10,16,18H,11H2,1H3/t16-/m1/s1

Upstream product

• 120-72-9 indole 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 95-20-5 2-methyl-1H-indole 

Downstream Products

• 203394-30-3 2-(1H-indol-3-yl)-2-(4-methoxyphenyl)ethanamine 

Relevant academic research and scientific papers

Design and synthesis of squaramide-based MOFs as efficient MOF-supported hydrogen-bonding organocatalysts

Herein, we utilize a new, squaramide-based ligand, combined with a postsynthetic exchange (PSE) synthetic approach to prepare a series of Cu(ii)-squaramide MOFs that are active catalysts for the Friedel-Crafts reaction.

Calix[6]arene-based Br?nsted acids for molecular recognition and catalysis

We report the synthesis of a versatile trifluoromethylsulfonamide calix[6]arene derivative with Br?nsted acid features which can influence both molecular recognition and catalytic application. Indeed, in low polarity media, the trifluoromethyl-containing

Regioselective and solvent-free arylation of β-nitrostyrenes with mono- and dialkyl anilines

A green and solvent-free method were developed for alkylation of N,N-dialkylanilines with substituted β-nitrostyrenes using 10?mol% of choline chloride-zinc chloride deep eutectic solvent at 70?°C. The reaction was highly regioselective and only para-substituted products have been prepared. Despite the sensitivity and weak reactivity of the aniline derivatives for the Friedel–Crafts reaction in acidic media, the presented procedure was successfully carried out this transformation. The synthetic protocol was expanded for the alkylation of pyrrole and indole to produce pharmaceutically active compounds. The reduction of the nitro group of the product to amine was performed using Pd/C and hydrazine to produce amphetamine structure.

Trisulfonamide calix[6]arene-catalysed Michael addition to nitroalkenes

We describe the application of a novel family of trisulfonamide (TSA) calix[6]arenes in general acid catalysis. Hydrogen-bonding interactions between acidic TSA and methanol boosted the reactivity of the Michael addition of indoles to nitroalkene derivati

One-Pot Synthesis of 3-(2-Fluoroalkenyl)indoles

An unprecedented one-pot synthesis of 3-(fluoroalkenyl)indoles was developed. This process involves a catalyst-free Michael addition of β-fluoro-β-nitrostyrenes to indoles in neat followed by elimination of HNO2 using DBU as a base. The effectiveness of this approach was demonstrated through the preparation of variety of target products in up to 75 % isolated yield.

Design of a Primary-Amide-Functionalized Highly Efficient and Recyclable Hydrogen-Bond-Donating Heterogeneous Catalyst for the Friedel-Crafts Alkylation of Indoles with β-Nitrostyrenes

A primary-amide-functionalized metal organic framework, {[Zn2(2-BQBG)(BDC)2]·10H2O}n (1) (in which 2-BQBG = 2,2′-(butane-1,4-diylbis((quinolin-2-ylmethyl)azanediyl))diacetamide and BDC = 1,4-benzenedicarboxylate

The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.

Electrostatically enhanced phosphoric acids and their applications in asymmetric friedel-crafts alkylations

A series of electrostatically enhanced phosphoric acid catalysts were synthesized and studied. These compounds possess two positively charged N-octylpyridinium or triarylphosphonium ion centers at the 3,3′-positions of the (R)-BINOL backbone to enhance re

Friedel-Crafts alkylation reaction with fluorinated alcohols as hydrogen-bond donors and solvents

An effective and clean FC alkylation of indoles and electron-rich arenes with β-nitroalkenes in HFIP was reported. The desired products are formed rapidly in excellent yields under mild conditions without the need for any additional catalysts or reagents. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives.

2D-2D Nanocomposite of MoS2-Graphitic Carbon Nitride as Multifunctional Catalyst for Sustainable Synthesis of C3-Functionalized Indoles

A nanocomposite of two-dimensional MoS2 supported on graphitic C3N4 nanosheets has been prepared by a facile ultrasonication method followed by demonstrating its ability to catalyze the synthesis of several indole derivatives. The as-prepared nanocomposite catalyst was characterized in detail by using different microscopic and spectroscopic techniques to understand its structure and physicochemical properties. Subsequently, this nanocomposite catalyst was used as a heterogeneous multifunctional catalyst to synthesize several C3-functionalized indoles in the aqueous medium. The employed strategy also provided very good catalyst recyclability and versatility for the synthesis of various precursors of medicinally significant indoles, such as serotonin, melatonin, and various β-carboline alkaloids. In addition, a natural product derivate has been prepared on the gram-scale by using this methodology. Furthermore, high atom economy (100 %) and lower E-factor (0.042) makes this strategy a sustainable approach for the synthesis of C3-functionalized indoles.