One-pot Three-component Synthesis of Furan-based Heterocycles from Benzyl Halides

被引：11

作者：

Beerappa, Mallappa ^{[1
]}

Shivashankar, Kalegowda ^{[1
]}

机构：

[1] Bangalore Univ, PG Dept Chem, Cent Coll Campus, Bangalore 560001, Karnataka, India

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2017年 / 54卷 / 04期

关键词：

INTRAMOLECULAR HYDROARYLATION; MULTICOMPONENT REACTION; BIOLOGICAL EVALUATION; AROMATIC-ALDEHYDES; NEO-TANSHINLACTONE; ANTITUMOR AGENTS; SELECTIVE METHOD; ALKYL-HALIDES; CANCER AGENTS; KEY REAGENTS;

D O I：

10.1002/jhet.2806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and a novel approach for the synthesis of furochromene and furopyran scaffolds are described. Benzyl halides undergo oxidation in Kornblum conditions to give the corresponding aldehydes, which in turn undergo [4+1] cycloaddition reaction with isocyanide to afford the corresponding furan derivatives. The significant attraction of this protocol is simple procedure, mild reaction condition, and good yield.

引用

页码：2197 / 2205

页数：9

共 49 条

[1] One-Pot Three-Component Synthesis of 4(3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2012, 23 (01) :85-88

[2] One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides [J].

Adib, Mehdi ;

Sheikhi, Ehsan ;

Rezaei, Narjes .

TETRAHEDRON LETTERS, 2011, 52 (25) :3191-3194

[3]

Alonso S. J., 2011, J ORG CHEM, V76, P1634

[4]

Babu S.P., 2012, PHARM CHEM, V4, P2178

[5] A Novel Approach for the Synthesis of Furopyrimidine and Oxobenzofuran Derivatives [J].

Bayat, Mohammad ;

Shiraz, Nader Zabarjad ;

Hosseini, Seyyed Hajar .

HELVETICA CHIMICA ACTA, 2010, 93 (11) :2189-2193

[6] Multicomponent reaction of benzyl halides: Synthesis of [1,2,4]triazolo/benzimidazolo quinazolinones [J].

Beerappa, Mallappa ;

Shivashankar, Kalegowda .

SYNTHETIC COMMUNICATIONS, 2016, 46 (05) :421-432

[7] One pot synthesis of pyran-based heterocycles from benzyl halides as key reagents [J].

Beerappa, Mallappa ;

Shivashankar, Kalegowda .

RSC ADVANCES, 2015, 5 (38) :30364-30371

[8] Synthesis of aromatic aldehydes by a fast method involving Kornblum's reaction [J].

Bratulescu, George .

SYNTHETIC COMMUNICATIONS, 2008, 38 (16) :2748-2752

[9] Total Syntheses of the Coumarin-Containing Natural Products Pimpinellin and Fraxetin Using Au(I)-Catalyzed Intramolecular Hydroarylation (IMHA) Chemistry [J].

Cervi, Aymeric ;

Aillard, Paul ;

Hazeri, Nourallah ;

Petit, Laurent ;

Chai, Christina L. L. ;

Willis, Anthony C. ;

Banwell, Martin G. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9876-9882

[10]

Chauder BA, 1999, ANGEW CHEM INT EDIT, V38, P1435, DOI 10.1002/(SICI)1521-3773(19990517)38:10<1435::AID-ANIE1435>3.0.CO

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