Metal free TBHP-promoted intramolecular carbonylation of arenes via radical cross-dehydrogenative coupling: synthesis of indenoquinolinones, 4-azafluorenones and fluorenones

被引：35

作者：

Mishra, Kalpana ^{[1
]}

Pandey, Ashok Kumar ^{[2
]}

Singh, Jay Bahadur ^{[1
]}

Singh, Radhey M. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Inst Sci, Ctr Adv Studies, Dept Chem, Varanasi 221005, Uttar Pradesh, India

[2] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 26期

关键词：

C-H ACTIVATION; AROMATIC-SUBSTITUTION BHAS; FACILE SYNTHESIS; BOND FORMATION; ANTIPROLIFERATIVE EVALUATION; EFFICIENT SYNTHESIS; ALDOXIME ETHERS; ARYL HALIDES; DERIVATIVES; ARYLATION;

D O I：

10.1039/c6ob00998k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free, TBHP-promoted economical route is developed via the sp(2) C-H bond functionalization strategy for the synthesis of indenoquinolinones, 4-azafluorenones and fluorenones. Reactions provided excellent yield of the products under mild conditions. We have successfully synthesized 11H-indeno [1,2-b]quinolin-11-one, an antibacterial agent, in excellent yields.

引用

页码：6328 / 6336

页数：9

共 71 条

[1] Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives:: A one-pot protocol to substituted azabiaryls
Alessi, Manlio
Larkin, Andrew L.
Ogilvie, Kevin A.
Green, Laine A.
Lai, Sunny
Lopez, Simon
Snieckus, Victor
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) : 1588 - 1594
[2] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[3] FeCl3•6H2O-catalyzed facile and efficient synthesis of pyrano[4,3-b]quinolines and isochromenes
Asthana, Mrityunjaya
Singh, Jay Bahadur
Singh, Radhey M.
[J]. TETRAHEDRON LETTERS, 2016, 57 (05) : 615 - 618
[4] Facile synthesis of functionalized 1H-pyrrolo[2,3-b]quinolines via Ugi four-component reaction followed by Cu-catalyzed aryl-amide, C-N bond coupling
Asthana, Mrityunjaya
Kumar, Ritush
Gupta, Tanu
Singh, Radhey M.
[J]. TETRAHEDRON LETTERS, 2015, 56 (07) : 907 - 912
[5] I2-catalyzed base-free cyclization of 3-homoallylquinoline-2-thiones: facile synthesis of tetracyclic, furothiopyrano[2,3-b]quinolines
Asthana, Mrityunjaya
Sharma, Neha
Kumar, Ritush
Singh, Jay Bahadur
Singh, Radhey M.
[J]. TETRAHEDRON LETTERS, 2014, 55 (31) : 4378 - 4381
[6] Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4:: Synthesis of benzocyclic ketones
Barluenga, Jose
Trincado, Monica
Rubio, Eduardo
Gonzalez, Jose M.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3140 - 3143
[7] The total synthesis of streptonigrin and related antitumor antibiotic natural products
Bringmann, G
Reichert, Y
Kane, VV
[J]. TETRAHEDRON, 2004, 60 (16) : 3539 - 3574
[8] Synthesis and evaluation as potential anticancer agents of novel tetracyclic indenoquinoline derivatives
Chakrabarty, Shubhashis
Croft, Michael S.
Marko, Melissa G.
Moyna, Guillermo
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (05) : 1143 - 1149
[9] Chemistry of acyl radicals
Chatgilialoglu, C
Crich, D
Komatsu, M
Ryu, I
[J]. CHEMICAL REVIEWS, 1999, 99 (08) : 1991 - 2069
[10] Synthesis of substituted indeno[1,2-b]quinoline-6-carboxamides, [1]benzothieno[3,2-b]quinoline-4-carboxamides and 10H-quindoline-4-carboxamides:: Evaluation of structure-activity relationships for cytotoxicity
Chen, JJ
Deady, LW
Desneves, J
Kaye, AJ
Finlay, GJ
Baguley, BC
Denny, WA
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (10) : 2461 - 2466

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