Synthesis of 2‐Alkenyl‐4H‐3,1‐Benzoxazin‐4‐Ones through HFIP‐Mediated Decarboxylative [4+2]‐Annulation of Isatoic Anhydrides with Cyclopropenones under Silver Catalysis

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(16), С. 4085 - 4090

Опубликована: Июнь 25, 2021

Abstract We herein describes an HFIP‐mediated [4+2]‐cycloaddition reaction from simple and easily available isatoic anhydrides cyclopropenones under silver catalysis. This transformation involves the tandem decarboxylative esterification, intermolecular addition, intramolecular substitution, small ring opening isomerization processes, which allows rapid assembly of versatile 2‐diarylalkenyl‐4 H ‐3,1‐benzoxazin‐4‐ones. magnified image

Язык: Английский

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Cascade Annulation for Synthesizing Chromenopyrrolones from o-Hydroxyphenyl Enaminones and 2-Halo-N-alkyloxyacetamides

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 27, 2024

A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-

Язык: Английский

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Selective Construction of Diverse Polycyclic Spirooxindoles via a Three-Component Reaction of Cyclic Mercapto-Substituted β-Enamino Esters, Isatins, and Cyclic 1,3-Diketones

The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(19), С. 12117 - 12127

Опубликована: Сен. 9, 2020

The three-component reaction of alkyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetates, isatins, and 1,3-indanedione (1,3-cyclopentanedione) in ethanol the presence acetic acid conveniently afforded spiro[indeno[1,2-b]phenothiazine-6,3′-indolines] or spiro[cyclopenta[b]phenothiazine-4,3′-indolines] good yields with high diastereoselectivity. More interestingly, a similar 4-hydroxychromen-2-one resulted unexpected polycyclic spiro[benzo[b]chromeno[3′,4′:5,6]pyrano[2,3-e][1,4]thiazine-7,3′-indolines] satisfactory yields. A plausible mechanism was rationally proposed for formation different kinds spiro compounds, stereochemistries various compounds were clearly elucidated.

Язык: Английский

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Base‐Promoted Synthesis of 3‐Alkenyl‐2‐pyridones from N‐Propargyl‐β‐enaminones and Aryl Aldehydes

Chinese Journal of Chemistry, Год журнала: 2021, Номер 39(10), С. 2781 - 2788

Опубликована: Июнь 27, 2021

Main observation and conclusion In this article, we report a base‐promoted sequential cyclization/aldol‐type condensation/isomerization cascade reaction of N ‐propargyl‐β‐enaminones with aryl aldehydes. The key step in protocol is the generation 1,4‐oxazepine anions from under basic conditions, which are captured by method allows formation one pyridone core C—C double bond “one pot”, preparation variety densely decorated derivatives moderate to good yields broad functional group tolerance.

Язык: Английский

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Metal-free synthesis of quinoline-2,4-dicarboxylate derivatives using aryl amines and acetylenedicarboxylates through a pseudo three-component reaction

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(32), С. 7041 - 7050

Опубликована: Янв. 1, 2021

An efficient, useful and one-pot protocol for the synthesis of quinoline-2,4-dicarboxylate scaffolds is accomplished from aryl amines dimethyl/diethyl acetylenedicarboxylates using 20 mol% molecular iodine as a catalyst in acetonitrile at 80 °C.

Язык: Английский

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