Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

被引：26
作者：
Albano, Gianluigi [1 ]
Aronica, Laura Antonella [1 ]
机构：
[1] Univ Pisa, Dept Chem & Ind Chem, Via G Moruzzi 13, I-56124 Pisa, Italy
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 06期
关键词：
phthalan; isoindoline; cyclization; transition-metal catalysis; Sonogashira reaction; CATALYZED 2+2+2 CYCLOADDITION; DIELS-ALDER REACTION; GARRATT-BRAVERMAN CYCLIZATION; DEHYDROGENASE KINASE INHIBITORS; CARBON TRIPLE BOND; ENANTIOSELECTIVE SYNTHESIS; ALKYNE CYCLOTRIMERIZATIONS; TERMINAL ALKYNES; GOLD CATALYSIS; ISOQUINOLINE DERIVATIVES;
D O I：
10.1055/s-0037-1609175
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxygen and nitrogen heterocycles are present in a vast number of natural substrates and biologically active molecules. In particular, phthalan and isoindoline subunits are found in many classes of products such as antibiotics, antioxidants, antimycotics, pigments, and fluorophores. Therefore several procedures dedicated to the construction of these heterocycles have been developed. In this review, a detailed analysis of the literature data regarding the synthesis of these nuclei via cyclization reactions is reported. 1 Introduction 2 Phthalans 2.1 Oxa-Pictet-Spengler Reaction 2.2 Garratt-Braverman Cyclization 2.3 Diels-Alder and Related Reactions 2.4 [2+2+2] Cyclotrimerization of Alkynes 2.5 Cycloetherification of ortho -Substituted Aromatics 2.6 Tandem Carbonylative Sonogashira Coupling-Cyclization Reactions 3 Isoindolines 3.1 Amination of Dihalides 3.2 Intramolecular Hydroamination 3.3 Diels-Alder and Related Reactions 3.4 [2+2+2] Cycloaddition Reactions 3.5 Tandem Carbonylative Sonogashira Coupling-Cyclization Reactions 4 Conclusions
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页码：1209 / 1227
页数：19
相关论文
共 232 条
[1]   A facile Garratt-Braverman cyclization route to intercalative DNA-binding bis-quinones [J].
Addy, Partha Sarathi ;
Dutta, Sansa ;
Biradha, Kumar ;
Basak, Amit .
TETRAHEDRON LETTERS, 2012, 53 (01) :19-22
[2]   Nitrogen-containing remote functionalised organolithium compounds by reductive opening of five- and six-membered heterocycles [J].
Almena, J ;
Foubelo, F ;
Yus, M .
TETRAHEDRON, 1996, 52 (25) :8545-8564
[3]   1,2-DI(LITHIOMETHYL)BENZENE FROM PHTHALAN - SEQUENTIAL INTRODUCTION OF 2 DIFFERENT ELECTROPHILES [J].
ALMENA, J ;
FOUBELO, F ;
YUS, M .
TETRAHEDRON, 1995, 51 (11) :3351-3364
[4]   Novel synthesis of isoindoline/isoindoline-1,3-dione derivatives under solventless conditions and evaluation with the human D2 receptor [J].
Andrade-Jorge, Erik ;
Bahena-Herrera, Jose R. ;
Garcia-Gamez, Jesus ;
Padilla-Martinez, Itzia I. ;
Trujillo-Ferrara, Jose G. .
MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (10) :2420-2431
[5]   Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases [J].
Arico, F. ;
Evaristo, S. ;
Tundo, P. .
GREEN CHEMISTRY, 2015, 17 (02) :1176-1185
[6]   Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions [J].
Aronica, Laura Antonella ;
Albano, Gianluigi ;
Giannotti, Luca ;
Meucci, Elisa .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (05) :955-963
[7]   Cyclocarbonylative Sonogashira Reactions of 1-Ethynylbenzyl Alcohols: Synthesis of 1-Carbonylmethylene-1,3-Dihydroisobenzofurans [J].
Aronica, Laura Antonella ;
Giannotti, Luca ;
Tuci, Giulia ;
Zinna, Francesco .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (22) :4944-4949
[8]   Iridium(III)-Catalyzed Approach for the Synthesis of Fused Arenes: Access to Isoindolines, Indanes, and Dihydroisobenzofurans [J].
Auvinet, Anne-Laure ;
Ez-Zoubir, Mehdi ;
Bompard, Savinien ;
Vitale, Maxime R. ;
Brown, Jack A. ;
Michelet, Veronique ;
Ratovelomanana-Vidal, Virginie .
CHEMCATCHEM, 2013, 5 (08) :2389-2394
[9]   Solvent-Free Iridium(III)-Catalyzed [2+2+2] Cycloaddition Providing Access to Fused Arenes: Isoindolines, Dihydroisobenzofurans and Indanes [J].
Auvinet, Anne-Laure ;
Michelet, Veronique ;
Ratovelomanana-Vidal, Virginie .
SYNTHESIS-STUTTGART, 2013, 45 (14) :2003-2008
[10]   Practical and Efficient Iridium Catalysis for Benzannulation: An Entry To Isoindolines [J].
Auvinet, Anne-Laure ;
Ez-Zoubir, Mehdi ;
Vitale, Maxime R. ;
Brown, Jack A. ;
Michelet, Veronique ;
Ratovelomanana-Vidal, Virginie .
CHEMSUSCHEM, 2012, 5 (10) :1888-1891
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