118488-74-7Relevant articles and documents
Microfluidic origami: A new device format for in-line reaction monitoring by nanoelectrospray ionization mass spectrometry
Kirby, Andrea E.,Wheeler, Aaron R.
, p. 2533 - 2540 (2013)
Microfluidics is an attractive platform for chemical synthesis because it offers fast reaction times, reduced reagent usage, and the ability to integrate multiple functions on a single device. Digital Microfluidics (DMF) is particularly well-suited for microscale chemical synthesis, as it permits discretized sample handling, allowing for total process control. However, a limitation of DMF-based synthesis is analysis, which is often performed offline. To this end, we have developed "microfluidic origami", a new device format that integrates DMF with in-line analysis by mass spectrometry (MS). This format comprises a DMF platform and a folded nanoelectrospray ionization (nanoESI) emitter formed on a single flexible polyimide film substrate. Additionally, the device contains a two-plate-to-one-plate DMF interface, which allows for straightforward coupling of micro-reaction operations and product delivery to the emitter for analysis. The integrated platform was used to perform the Morita-Baylis-Hillman (MBH) reaction using DMF followed by inline MS analysis for monitoring the reaction progress in real-time. We propose that this platform has potential as a new tool for real-time monitoring of reaction rates and reaction pathways and could be a useful addition to the synthetic organic chemistry laboratory.
Propylphosphonic acid anhydride–mediated amidation of Morita–Baylis–Hillman–derived indolizine-2-carboxylic acids
Sekgota, Khethobole C,Isaacs, Michelle,Hoppe, Heinrich C,Seldon, Ronnett,Warner, Digby F,Khanye, Setshaba D,Kaye, Perry T
, p. 674 - 678 (2021)
Propylphosphonic acid anhydride has been successfully used as a coupling agent in the synthesis of a series of indolizine-2-carboxamido derivatives from indolizine-2-carboxylic acid and its 3-acetylated analogue. The acid substrates were obtained by sapon
Microwave-assisted convenient syntheses of 2-indolizine derivatives from Morita-Baylis-Hillman adducts: New in silico potential ion channel modulators
Cunha, Saraghina M.D.,De Oliveira, Ramon G.,Vasconcellos, Ma?rio L.A.A.
, p. 432 - 438 (2013)
In this work, a microwave-assisted synthesis study by microwave irradiation to produce indolizine-2-carbonitrile and indolizine-2-carboxylate in good to high yields (70 and 81percent, respectively) in one step from Morita-Baylis-Hillman adducts (MBHA) is presented. These compounds were subsequently transformed to high yields (94 to 100percent, respectively) in three 2-indolizine derivatives. The five synthesized compounds were designed in silico aiming to present potential selective activities as ion channel modulators. These activities were suggested by the score values using Molinspiration Cheminformatics program.
An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope
Camilo, Nilton S.,Santos, Hugo,Zeoly, Lucas A.,Fernandes, Fábio S.,Rodrigues, Manoel T.,Silva, Thiago S.,Lima, Samia R.,Serafim, José Cláudio,de Oliveira, Aline S. B.,Carpanez, Arthur G.,Amarante, Giovanni W.,Coelho, Fernando
supporting information, (2022/01/22)
The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important C?C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic par
Chiral Phosphoric Acid Catalyzed Desymmetrization of Cyclopentendiones via Friedel–Crafts Conjugate Addition of Indolizines
Ni, Qijian,Zhu, Zhiming,Fan, Yanjun,Chen, Xiaoyun,Song, Xiaoxiao
supporting information, p. 9548 - 9553 (2021/12/14)
An organocatalytic highly diastero- and enantioselective Friedel–Crafts conjugate addition of indolizines to prochiral cyclopentenediones has been successfully developed. This desymmetric transformation provides a direct access to the desired indolizine-substituted cyclopentanediones in yields of 62–91% and excellent stereoselectivities. The utility of the approach was demonstrated by diverse late-stage functionalizations through reduction or oxidation. Importantly, the direct sp2 C–H functionalization with nitromethane in one-pot process resulted in the indolizine-linked axially chiral styrene bearing a remote chiral center.
