Synthesis of naturally occurring seven-membered nitrogen heterocycles and related bioactive compounds DOI
Laura Adarve-Cardona, Alexander Garay‐Talero, Diego Gamba‐Sánchez

et al.

Studies in natural products chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 189 - 235

Published: Jan. 1, 2023

Language: Английский

Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature DOI
Arnab Ghosh, Rajeev V. Hegde, Haridas B. Rode

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(21), P. 8189 - 8193

Published: Oct. 13, 2021

An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer formation new C═O, C-N, C-O bonds occur at room temperature to form six-, seven-, eight-membered heterocycles one-pot reaction without using an external oxidant base. The photophysical properties are studied ultraviolet-visible absorption photoluminescence. mechanistic elucidation well supported by control experiment literature precedents.

Language: Английский

Citations

8
One-Pot Synthetic Approach to 3-Carboxyl- and 3-Ketopyridines in Aqueous Media DOI

Aleksander R. Bena,

Evangelos G. Bakalbassis,

Michail M. Sigalas

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8055 - 8068

Published: June 13, 2023

We describe a one-pot strategy to access 3-carboxyl- and 3-ketopyridines from readily available alkynes propargylamine via hydroamination process. This protocol uses as starting materials, has broad substrate scope, operates in aqueous media open-air conditions. A series of aryl- alkyl-substituted pyridines were synthesized. green methodology can be scaled laboratory size was used for the synthesis natural product core, 4-aza-fluorenone. Density-functional theory control mechanistic studies support domino hydroamination/pericyclic reaction, which includes formation enaminone intermediate its transformation through an aza-Claisen rearrangement desired pyridine product.

Language: Английский

Citations

3
Electrophilic carbocyclization reactions of 2-(2-alkynylphenyl)amino-1,4-naphthoquinones DOI

Chang-You Sie,

Che‐Ping Chuang

Organic & Biomolecular Chemistry, Journal Year: 2018, Volume and Issue: 16(30), P. 5483 - 5491

Published: Jan. 1, 2018

Electrophilic carbocylization reactions for the synthesis of 5H-benzo[b]naphtho [2,3-f]azepine-6,11-diones are described.

Language: Английский

Citations

6
A facile one-pot synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines DOI
Elif Serel Yilmaz, Metin Zora

Synthetic Communications, Journal Year: 2020, Volume and Issue: 51(5), P. 709 - 719

Published: Nov. 26, 2020

An unprecedented method for the synthesis of 2-(prop-2-yn-1-ylidene)-2,3-dihydro-1,4-thiazepines from N-(2,4-pentadiynyl) β-enaminones is reported. Upon treatment with Lawesson's reagent, were thionated to furnish β-enaminothiones, which immediately underwent 7-exo-dig cyclization generate in one-pot. A general trend was observed various and proceeded broad functional group tolerance. This operationally easy may provide quick access a library functionalized 1,4-thiazepines field pharmaceutical chemistry.

Language: Английский

Citations

6
Synthesis of naturally occurring seven-membered nitrogen heterocycles and related bioactive compounds DOI
Laura Adarve-Cardona, Alexander Garay‐Talero, Diego Gamba‐Sánchez

et al.

Studies in natural products chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 189 - 235

Published: Jan. 1, 2023

Language: Английский

Citations

2