Synthesis of 1H-Inden-1-ylidenes via Carboannulation of Internal Alkynes with (E)-3-(2-Bromophenyl) Acrylaldehyde: Potential Precursors for Drug Development

被引：4

作者：

Dhanorkar, Ritesh J. ^{[1
]}

Gupta, Virendra Kumar ^{[1
]}

Gocher, Chandra Prakash ^{[1
]}

机构：

[1] Reliance Ind Ltd, Reliance Res & Dev Ctr, Polymer Synth & Catalysis, Navi Mumbai 400701, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 8卷 / 06期

关键词：

1H-inden-1-ylidene; Carboannulation; internal alkynes; (E)-3-(2-bromophenyl) acrylaldehyde; Palladium; INDENE DERIVATIVES; CATALYZED TANDEM; COUPLING REACTIONS; CYCLIZATION; ANNULATION;

D O I：

10.1002/ajoc.201900183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1H-Inden-1-ylidene derivatives have been synthesized using a simple and efficient Pd-catalyzed annulation of functionalized (E)-3-(2-bromophenyl) acrylaldehyde with internal alkynes. The proposed mechanism involves an oxidative addition and carbopalladation of an alkyne to generate a vinyl palladium intermediate followed by beta-hydrogen elimination. These pre-functionalized indene-based cyclic precursors can be potential bioactive systems for drug discovery and development.

引用

页码：909 / 915

页数：7

共 47 条

[1] Effect of the nature of metallocene complexes of group IV metals on their performance in catalytic ethylene and propylene polymerization [J].

Alt, HG ;

Köppl, A .

CHEMICAL REVIEWS, 2000, 100 (04) :1205-1221

[2] Synthesis of Diverse Indene Derivatives from 1-Diazonaphthalen-2(1H)-ones via Thermal Cascade Reactions [J].

Bahadur, Krishna ;

Magar, Somai ;

Lee, Yong Rok .

ORGANIC LETTERS, 2013, 15 (17) :4288-4291

[3]

BECKER CL, 1991, SYNLETT, P642

[4] A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes [J].

Challa, Chandrasekhar ;

Vellekkatt, Jamsheena ;

Ravindran, Jaice ;

Lankalapalli, Ravi S. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (43) :8588-8592

[5] Cobalt-catalyzed regioselective carbocyclization reaction of o-iodophenyl ketones and aldehydes with alkynes, acrylates, and acrylonitrile:: A facile route to indenols and indenes [J].

Chang, KJ ;

Rayabarapu, DK ;

Cheng, CH .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (14) :4781-4787

[6]

Coumbis A. E., 2005, MOLECULES, V10, P1340

[7] FeCl3 Catalyzed Prins-Type Cyclization for the Synthesis of Highly Substituted Indenes: Application to the Total Synthesis of (±)-Jungianol and epi-Jungianol [J].

Dethe, Dattatraya H. ;

Murhade, Ganesh .

ORGANIC LETTERS, 2013, 15 (03) :429-431

[8] Recent Advances in the Synthesis of Indanes and Indenes [J].

Gabriele, Bartolo ;

Mancuso, Raffaella ;

Veltri, Lucia .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (15) :5056-5094

[9] Palladium-catalyzed synthesis of indene derivatives via propargylic carbonates with in situ generated organozinc compounds [J].

Guan, Zheng-Hui ;

Ren, Zhi-Hui ;

Zhao, Lian-Biao ;

Liang, Yong-Min .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (06) :1040-1045

[10] Synthesis of the putative structure of eupomatilone-6 [J].

Gurjar, MK ;

Cherian, J ;

Ramana, CV .

ORGANIC LETTERS, 2004, 6 (03) :317-319

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