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 43 条

[1] Pd(0)-catalyzed intramolecular Heck reaction: A general route for fused oxepine derivatives [J].

Adak, Arup Kumar ;

Mandal, Arabinda ;

Manna, Susanta Kumar ;

Mondal, Suresh Kumar ;

Jana, Akash ;

Ghosh, Dipesh ;

Kundu, Debasish ;

Samanta, Shubhankar ;

Ray, Jayanta K. .

SYNTHETIC COMMUNICATIONS, 2016, 46 (05) :452-459

[2] Environmentally-friendly synthesis, structural determination and antimicrobial activity of new class of spiropyrrolidine embedded with indenoquinoxaline and chromanone heterocyclic units [J].

Arumugam, Natarajan ;

Soliman, Saied M. ;

Viswanathan, Vijayan ;

Almansour, Abdulrahman I. ;

Kumar, Raju Suresh ;

Mahalingam, Sakkarapalayam M. ;

Krishnamoorthy, Bellie Sundaram ;

Dege, Necmi ;

Karuppiah, Ponmurugan ;

Perumal, Karthikeyan .

JOURNAL OF MOLECULAR STRUCTURE, 2023, 1293

[3] Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide [J].

Athira, Mohanakumaran ;

Shanmugam, Ponnusamy .

SYNOPEN, 2021, 05 (01) :17-24

[4] Synthesis of blue emissive functionalized 9,9-disubstituted fluorene derivatives via BF3•OEt2 mediated reaction of co-planar 9-(phenylethynyl)-9H-fluoren-9-ols with isatin imines [J].

Athira, Mohanakumaran ;

Meerakrishna, Ramakrishnan Suseela ;

Shanmugam, Ponnusamy .

NEW JOURNAL OF CHEMISTRY, 2020, 44 (16) :6652-6660

[5] Recent synthetic strategies toward the synthesis of spirocyclic compounds comprising six-membered carbocyclic/heterocyclic ring systems [J].

Babar, Kashaf ;

Zahoor, Ameer Fawad ;

Ahmad, Sajjad ;

Akhtar, Rabia .

MOLECULAR DIVERSITY, 2021, 25 (04) :2487-2532

[6] Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidines] [J].

Barkov, Aleksey Yi. ;

Zimnitskiy, Nikolay S. ;

Korotaev, Vladislav Yu. ;

Kutyashev, Igor B. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Ya. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (04) :451-459

[7] Unexpected regiochemistry in [3+2] cycloaddition reaction of azomethine ylides of indenoquinoxalinone series to arylidene malononitriles [J].

Barkov, Alexey Yu ;

Zimnitskiy, Nikolay S. ;

Kutyashev, Igor B. ;

Korotaev, Vladislav Yu ;

Sosnovskikh, Vyacheslav Ya .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (01) :43-50

[8]

Baudy R B., 1994, Expert Opin. Ther. Pat, V4, P1173

[9]

Bentz D, 2000, SYNTHESIS-STUTTGART, P1766

[10] Recent Advances in One-Pot Enyne Metathesis Processes for the Preparation of Biologically and Medicinally Relevant Compounds [J].

Bernardi, Eric ;

Colombo, Lino ;

Serra, Massimo .

SYNTHESIS-STUTTGART, 2021, 53 (05) :785-804

← 1 2 3 4 5 →