Copper Sulfate (CuSO4): An Efficient Reagent in Organic Synthesis DOI Creative Commons

Housemberg D. S. Ferrreira,

Euzébio Guimarães Barbosa, Alessandro K. Jordão

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(03), P. 371 - 373

Published: July 21, 2023

Abstract

Language: Английский

“Back‐to‐Front” Indole and Carbazole Synthesis from N,N‐Bis‐(2‐bromoallyl)amines by Combining Carbolithiation Reactions with Gold‐Catalysis DOI Creative Commons
Miguel Ángel Muñoz, Fernando Martínez, Marta Solas

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(21), P. 3716 - 3724

Published: Sept. 24, 2022

Abstract The combination of organolithium chemistry with gold catalysis has enabled the development a synthetic strategy for accessing polysubstituted indoles and carbazoles from readily available starting materials. This method is based on “back‐to‐front” approach ketopyrroles, generated by intramolecular carbolithiation N,N ‐bis‐(2‐lithioallyl)amines that evolve into 3,4‐bis(lithiomethyl)dihydropyrrole intermediates capable reacting carboxylic esters Weinreb amides. These ketopyrroles have demonstrated to be excellent precursors mono or bis(alkynols)pyrroles that, under gold‐catalysis, experience benzannulation reaction providing access regioselectively substituted carbazoles. magnified image

Language: Английский

Citations

8
Gram-Scale Total Synthesis of Carbazomycins A–D through Late-Stage Regioselective Demethylation of Aryl Methyl Ethers DOI

Yuxuan Feng,

Atsunori Mori, Kentaro Okano

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13472 - 13484

Published: Sept. 5, 2024

Gram-scale total synthesis of carbazomycins A-D is described. The carbazomycin A was achieved in 44% overall yield over six steps from symmetrical 5-chloro-1,2,3-trimethoxybenzene. key aryne-mediated carbazole formation and methylation provided the multiply substituted carbazole. regioselective demethylation trimethoxycarbazole performed using boron trichloride. Thereafter, phenolic hydroxy group converted into methyl to provide A. Subsequent installation methoxy realized D. Regioselective 1-dodecanethiol, effecting conversions D B C, respectively.

Language: Английский

Citations

0
Carbazoquinocin Analogues as Small Molecule Biomimetic Organocatalysts in Dehydrogenative Coupling of Amines DOI

Samrat Kundu,

Chayan Ghosh,

Abhisek Metya

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1705 - 1710

Published: Feb. 19, 2024

A new series of carbazole-cored biomimetic

Language: Английский

Citations

0
The Green Synthesis of 2‐Pyrrolin‐5‐ones from Bio‐renewable Glyoxal, Diketones and Amines DOI
Aanuoluwapo O. Oyejobi, Dandan Gao, Jiahua Wang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 21, 2024

Abstract Described herein is an effective and green reaction between diketones, amines bio‐renewable glyoxal, affording a wide range of 2‐pyrrolin‐5‐ones releasing water as the only byproduct. The features step‐economy, high efficiency, mild conditions, broad substrate scope, hazardous waste avoiding easy scale‐up. further transformation products aldehydes can be potentially applied for fluorescent dye synthesis.

Language: Английский

Citations

0
Copper Sulfate (CuSO4): An Efficient Reagent in Organic Synthesis DOI Creative Commons

Housemberg D. S. Ferrreira,

Euzébio Guimarães Barbosa, Alessandro K. Jordão

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(03), P. 371 - 373

Published: July 21, 2023

Abstract

Language: Английский

Citations

0