Synthesis of Indenoquinoxalinone-5-(furano, pyrano, and oxepino)spiro Ethers from Alkenylated Propargyl Ethers of Indenoquinoxalinone via Ring-Closing Enyne Metathesis

被引：0

作者：

Padmashrija, Ammundi Jayavel Chirranjeevi ^{[1
]}

Kannadasan, Sathananthan ^{[1
]}

Shanmugam, Ponnusamy ^{[2
]}

机构：

[1] Vellore Inst Technol, Sch Adv Sci, Dept Chem, Vellore 632014, India

[2] CSIR, Cent Leather Res Inst CLRI, Organ & Bioorgan Chem Div, Chennai 600020, India

来源：

SYNLETT | 2025年

关键词：

ring-closing enyne metathesis; indenoquinoxalinone; alkenyl ether; Grubbs II catalyst; oxacyclic spiro compounds; AZOMETHINE YLIDES; COPLANAR 9-(PHENYLETHYNYL)-9H-FLUOREN-9-OLS; 1,3-DIPOLAR CYCLOADDITION; FLUORENE DERIVATIVES; OLEFIN METATHESIS; CONSTRUCTION; 3-COMPONENT; ACCESS; TANDEM;

D O I：

10.1055/a-2489-7403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthetic route for indenoquinoxalinone spiro-oxacyclic systems with small to medium ring sizes has been developed via an efficient ring-closing enyne metathesis (RCEYM) as a key step. The starting material O-alkylated propargylic alcohol of indenoquinoxalinone is synthesized via a two-step protocol: 1. propargylation of ketone followed by 2. alkenylation of the resulting propargyl ethers with alkenyl bromides. Upon being subjected to RCEYM using Grubbs II catalyst, the resulting O-alkenylated propargyl derivative furnished the spiro-ethereal products in good yield. Spectroscopic data and single-crystal XRD analysis characterized the structures of the products. A plausible mechanism is provided.

引用

页数：8

共 10 条

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MOLBANK, 2023, 2023 (01)
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