Formation of β-cyano-ketones through cyanide-promoted ring-opening of cyclic organic carbonates

文献信息

发布日期 2021-06-14

DOI 10.1039/D1QO00770J

影响因子 5.281

作者

Jixiang Ni, Àlex Cristòfol

查看原文

摘要

Here we disclose a method for the unexpected decarboxylative cyanide-assisted ring-opening reaction of a series of vinyl cyclic carbonates. At elevated temperature, the attack of a cyanide nucleophile at the methylenic carbon center of the organic carbonate is promoted which leads to the release of CO2 and MeCN and the intermediacy of a Michael acceptor that undergoes facile 1,4-addition affording a β-cyano ketone product. This chemistry features a rare ring-opening reaction that is not initiated at the typically more electrophilic carbonate carbonyl.

期刊推荐

Pharmaceutical Chemistry Journal

Applied Surface Science

Bulletin of Materials Science

Annual Review of Public Health

Tetrahedron Letters

European Journal of Medicinal Chemistry

Organic Geochemistry

Dental Materials

Journal of Dispersion Science and Technology

Applied Clay Science

来源期刊

Organic Chemistry Frontiers

CiteScore: 7.8

自引率: 8.7%

年发文量: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Formation of β-cyano-ketones through cyanide-promoted ring-opening of cyclic organic carbonates

文献信息

期刊推荐

相关文献

Inhibition of SC4MOL and HSD17B7 shifts cellular sterol composition and promotes oligodendrocyte formation

Natural product scaffolds as inspiration for the design and synthesis of 20S human proteasome inhibitors

Hyaluronan (HA)-inspired glycopolymers as molecular tools for studying HA functions

Bypassing the requirement for aminoacyl-tRNA by a cyclodipeptide synthase enzyme

In vivo modulation of ubiquitin chains by N-methylated non-proteinogenic cyclic peptides

Back cover

Fluorescent small-molecule agonists as follicle-stimulating hormone receptor imaging tools

Faster, better, and cheaper: harnessing microfluidics and mass spectrometry for biotechnology

Continuous direct anodic flow oxidation of aromatic hydrocarbons to benzyl amides

Site-specific modification and segmental isotope labelling of HMGN1 reveals long-range conformational perturbations caused by posttranslational modifications

您可能还喜欢

4-[[6-（3-苯基苯基）-7H-嘌呤-2-基]氨基]苯磺酰胺(CAS号：2079895-42-2)适用哪些法规指南？

反式-度骨化醇(CAS号：74007-20-8)的物理化学性质是什么？

莲花掌苷(CAS号：59282-56-3)的市场或研究趋势如何？

2-溴-6-(吡咯烷-1-基)吡啶-4-硼酸频那醇酯(CAS号：1150271-64-9)应用于哪些行业？

什么是methyl 2-(4-bromophenyl)-3-methylbutanoate(CAS号：1061284-70-5)？

CJC1-295(CAS号：863288-34-0)的物理化学性质是什么？

三正丁基锍碘(CAS号：18146-62-8)的市场或研究趋势如何？

雌二醇-[13C3]同位素内标(CAS号：1261254-48-1)通常如何合成？

N1-(2-吡啶甲基)-N2-(2-甲基-1-萘基)草酰胺(CAS号：2611225-93-3)的物理化学性质是什么？

如何处理含有十五碳烯酸甲酯(顺-10)(C15:1)标准品(CAS号：90176-52-6)的废料？

来源期刊

Organic Chemistry Frontiers

推荐化合物

11-Dodecyn-1-ol

Chloromethyl ethyl carbonate

3-Piperazinopropylmethyldimethoxysilane

1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione

N-[(Benzyloxy)carbonyl]serine

推荐供应商