A facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones

被引：83

作者：

Akram, Manjur O. ^{[1
,2
]}

Bera, Saibal ^{[2
,3
]}

Patil, Nitin T. ^{[1
,2
]}

机构：

[1] CSIR Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

[3] CSIR Natl Chem Lab, Phys & Mat Chem Div, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 83期

关键词：

C-H ALKYNYLATION; HIGHLY SUBSTITUTED FURANS; HYPERVALENT IODINE REAGENTS; ROOM-TEMPERATURE; ETHYNYL BENZIODOXOLONES; MULTICOMPONENT REACTION; CHELATION-ASSISTANCE; TANDEM REACTION; IONIC LIQUIDS; BOND-CLEAVAGE;

D O I：

10.1039/c6cc07119h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A strategy based on tandem alkynylation of o-hydroxyarylenaminones followed by intramolecular cyclization has been developed to generate a diverse array of 3-alkynyl chromones. The functionality embedded in these key intermediates enables their facile elaboration into more diverse structures by a variety of functionalizations and ring-forming processes.

引用

页码：12306 / 12309

页数：4

共 66 条

[1] Rh(III)- or Ir(III)-catalyzed ynone synthesis from aldehydes via chelation-assisted C-H bond activation [J].

Ai, Wen ;

Wu, Yunxiang ;

Tang, Huanyu ;

Yang, Xueyan ;

Yang, Yaxi ;

Li, Yuanchao ;

Zhou, Bing .

CHEMICAL COMMUNICATIONS, 2015, 51 (37) :7871-7874

[2] Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction [J].

Awuah, Emelia ;

Capretta, Alfredo .

ORGANIC LETTERS, 2009, 11 (15) :3210-3213

[3] 7-[3-(1-Piperidinyl)propoxy]chromenones as potential atypical antipsychotics [J].

Bolos, J ;

Gubert, S ;

Anglada, L ;

Planas, JM ;

Burgarolas, C ;

Castello, JM ;

Sacristan, A ;

Ortiz, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) :2962-2970

[4] Synthesis of 4-Aminoxanthones by an Uncatalyzed, Multicomponent Reaction [J].

Bornadiego, Ana ;

Diaz, Jesus ;

Marcos, Carlos F. .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (04) :718-722

[5] Electrophilic alkynylation: the dark side of acetylene chemistry [J].

Brand, Jonathan P. ;

Waser, Jerome .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (11) :4165-4179

[6] Ethynyl Benziodoxolones for the Direct Alkynylation of Heterocycles: Structural Requirement, Improved Procedure for Pyrroles, and Insights into the Mechanism [J].

Brand, Jonathan P. ;

Chevalley, Clara ;

Scopelliti, Rosario ;

Waser, Jerome .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (18) :5655-5666

[7] Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines [J].

Brand, Jonathan P. ;

Waser, Jerome .

ORGANIC LETTERS, 2012, 14 (03) :744-747

[8] One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines [J].

Brand, Jonathan P. ;

Chevalley, Clara ;

Waser, Jerome .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :565-569

[9] Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].

Brand, Jonathan P. ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307

[10] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

← 1 2 3 4 5 6 7 →