Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles

被引：51

作者：

Selvi, Thangavel ^{[1
]}

Srinivasan, Kannupal ^{[1
]}

机构：

[1] Bharathidasan Univ, Sch Chem, Tiruchirappalli 620024, Tamil Nadu, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 08期

关键词：

ADDITION-CYCLIZATION REACTIONS; DONOR-ACCEPTOR CYCLOPROPANES; 2+1 CYCLOADDITION REACTIONS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; NITROCYCLOPROPANES; ETHENETRICARBOXYLATES; CONSTRUCTION;

D O I：

10.1021/jo402848v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates, upon treatment with BF3 center dot OEt2, undergo ring-opening rearrangement and the Nef reaction to give aroylmethylidene malonates. The products are found to be potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.

引用

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页码：3653 / 3658

页数：6

共 5 条

[1] Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines
Sathishkannan, Gopal
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Srinivasan, Kannupal
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (06) : 1400 - 1406
[2] Synthesis of 2,4,5-trisubstituted oxazoles through tin(IV) chloride-mediated reaction of trans-2-aryl-3-nitro-cyclopropane-1,1-dicarboxylates with nitriles
Selvi, Thangavel
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CHEMICAL COMMUNICATIONS, 2014, 50 (74) : 10845 - 10848
[3] 2-Aryl-3,4-dihydropyrans as building blocks for organic synthesis: ring-opening reactions with nucleophiles
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Gu, Yanlong
TETRAHEDRON, 2011, 67 (43) : 8314 - 8320
[4] Lewis Acid-Mediated Ring-Opening Reactions of trans-2-Aroyl-3-styrylcyclopropane-1,1-dicarboxylates: Access to Cyclopentenes and E,E-1,3-Dienes
Thangamani, Murugesan
Srinivasan, Kannupal
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 571 - 577
[5] Boron Trifluoride-Promoted Indium(III) Triflate-Catalyzed Sequential One-Pot Synthesis of (1,2-Diaryl-2-oxoethyl)malonates from trans-2-Aryl-3-nitrocyclopropane-1,1-dicarboxylates and Activated Arenes
Selvi, Thangavel
Srinivasan, Kannupal
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2111 - 2118

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