Synthesis of chiral 1,3-dihydroisobenzofurans (phthalans) containing functional substituents in the 1-position

Dem'yanovich, V. M.; Shishkina, I. N.; Кузнецова, А. А.; Potekhin, K. A.; Chesnova, A. V.

doi:10.1134/s1070428006070104

Cited by 8 publications

(4 citation statements)

References 3 publications

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“…[6] In addition, alkylidenephthalans can give access to a variety of heterocycles, such as functionalized phenanthro [10,1-bc]furans, [7] isoquinolin-1(2H)-ones, [8] and pyrazoles [9] (Scheme 1). Although many procedures for phthalans preparation have been developed, [10] including reduction of phthalides, [11] hydrogenation of isobenzofurans, [12] Garratt-Braverman cyclizations, [13] oxa-Pictet-Spengler reactions [14] and cycloadditions (in particular Diels-Alder [15] or [2+2+2] cyclotrimerization of alkynes [16] ), the most common is based on cycloetherification of benzyl alcohols (or their derivatives) having an appropriate ortho-substituent: epoxides, [17] oxetanes, [18] quaternary ammonium salts, [19] benzyl halides or alcohols, [20] alkenes [21] and, in the specific case of 1-alkylidene-1,3dihydroisobenzofurans synthesis, also 1,2,3-triazole rings [22] and alkyne groups. The cyclisation of ortho-alkynyl O-benzyl-functionalized aromatics can be promoted by means of a base.…”

Section: Applications Reactivity and General Synthetic Methodsmentioning

confidence: 99%

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Albano

Aronica

2017

Eur J Org Chem

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Oxygen and Nitrogen-heterocyclic compounds are found in a vast number of natural substrates and biologically active molecules. In particular, phthalan, isochroman and isoindoline scaffolds are present in many classes of products such as antimicotics, antibiotics, antioxidants, pigments and fluorophores. Therefore several procedure dedicated to the buiding of such heterocycles have been developed. In this review a detailed analysis of literature data regarding these nuclei is described. Particular attention has been devoted to their biological and chemical potentialities and a deep investigation on the most important synthetic methods is reported. Cyclocarbonylative Sonogashira reaction of suitable alcohols and amides has been especially considered, since it represents a valuable and atom economic route to construct alkylidene phthalans, isochromans and isoindolines.Gianluigi Albano, born in Bari (Italy) in 1989, studied Chemistry at the University of Pisa (Italy), where he received his Master's Degree in February 2015. In November 2015 he started his PhD studies at the same university, under the supervision of Prof. Lorenzo Di Bari and Dr. Laura Antonella Aronica. His main research topics are focused on the synthesis and characterization of chiral conjugated oligomers for innovative optoelectronic applications and on the development of new protocols for the synthesis of heterocyclic compounds through transition metals-promoted reactions.Laura Antonella Aronica graduated cum laude in Chemistry in 1995 from the University of Pisa. In 1999 she obtained her Ph.D. in Chemical Sciences. During this period she spent six months as research assistant at University of Ottawa with Prof. Howard Alper. She is presently a researcher at the University of Pisa and her major research interests are concerned with organometallic chemistry directed towards organic synthesis and in particular with carbonylative cross coupling reactions and their application to the synthesis of heterocyclic compounds.

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Section: Applications Reactivity and General Synthetic Methodsmentioning

confidence: 99%

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Albano

Aronica

2017

Eur J Org Chem

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“…The most common synthetic approach to phthalans is based on the cycloetherification of benzyl alcohols (or also their derivatives, such as benzaldehydes and benzyl alkoxides generated in situ) having an appropriate ortho-substituent. Although several ortho-groups have been investigated including epoxides, 87 oxetanes, 88 1,2,3-triazole rings, 89 quaternary ammonium salts, 90 benzyl halides or alcohols, 91 and alkenes, 92 of particular interest is the 5-exo-dig cyclization of ortho-alkynyl O-benzyl-functionalized aromatics 69 to give 1-alkylidenephthalans 70 (Scheme 22), which cannot be obtained by the previously discussed methodologies. The reaction is generally promoted by a stoichiometric amount of base or catalytic amounts of a metal catalyst.…”

Section: Cycloetherification Of Ortho-substituted Aromaticsmentioning

confidence: 99%

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

Albano

Aronica

2018

Synthesis

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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 Introduction2 Phthalans2.1 Oxa-Pictet–Spengler Reaction2.2 Garratt–Braverman Cyclization2.3 Diels–Alder and Related Reactions2.4 [2+2+2] Cyclotrimerization of Alkynes2.5 Cycloetherification of ortho-Substituted Aromatics2.6 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions3 Isoindolines3.1 Amination of Dihalides3.2 Intramolecular Hydroamination3.3 Diels–Alder and Related Reactions3.4 [2+2+2] Cycloaddition Reactions3.5 Tandem Carbonylative Sonogashira Coupling–Cyclization Reactions4 Conclusions

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“…[63][64][65][66] Mainly, phthalan derivatives of 1,3-dihydroisobenzofuran are identified to show an extensive range of drug-like characteristics, like potent anti-oxidant, antidepressant, anti-histaminic, anti-inflammatories, and anti-fungal properties. [67,68] Pharmaceuticals such as Citalopram (29), [69] and Talopram (30), [70] act as powerful selective serotonin reuptake and norepinephrine transporters inhibitors, respectively. [69,[71][72][73] Few 1,3-dihydroisobenzofuran derivatives can inhibit cholines-terase (31), [74] cancer cell proliferation (32), [75] and peptide deformylase.…”

Section: Introductionmentioning

confidence: 99%

“…The 1,3‐dihydroisobenzofuran nucleus ( 2 ) (Figure 1) can be seen in several natural products and synthetic molecules with a variety of biological functions [63–66] . Mainly, phthalan derivatives of 1,3‐dihydroisobenzofuran are identified to show an extensive range of drug‐like characteristics, like potent anti‐oxidant, anti‐depressant, anti‐histaminic, anti‐inflammatories, and anti‐fungal properties [67,68] . Pharmaceuticals such as Citalopram ( 29 ), [69] and Talopram ( 30 ), [70] act as powerful selective serotonin reuptake and norepinephrine transporters inhibitors, respectively [69,71–73] .…”

Section: Introductionmentioning

confidence: 99%

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

et al. 2022

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The 2,3-dihydrobenzofuran heterocyclic systems are found in various biologically active natural and pharmaceutical products of biological relevance such as Phalarine, Rocaglamide, and Furaquinocin A. The interest in the study of 2,3-dihydrobenzofurans is constantly increasing because of their numerous biological properties such as anti-tumor, anticancer, anti-tubercular, and anti-malarial activities. Different methods have been established towards the synthesis of 2,3dihydrobenzofurans involved via intra-and inter-molecular reactions. Besides, the 1,3-dihydroisobenzofuran structure has been identified as a fundamental nucleus in many natural products, bioactive compounds, and functional molecules (e. g., Pestacin, Isopestacin, Citalopram, Xylarinol B, Matriisobenzofuran, Thunberginol F7-O-β-D-glucopyranoside). On the other hand, 1,3-disubstituted isobenzofurans are powerful structural motifs with a wide range of biological activities, like anti-inflammatory, anti-histaminic, and anti-HIV. In the last few years, a decent number of diligent synthetic approaches have been demonstrated toward synthesizing 1,3-disubstituted isobenzofurans. This review focuses on the effective synthetic routes developed to construct 2,3-dihydrobenzofurans and 1,3-dihydroisobenzofurans and their applications in recent years.

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Synthesis of chiral 1,3-dihydroisobenzofurans (phthalans) containing functional substituents in the 1-position

Cited by 8 publications

References 3 publications

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

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Synthesis of chiral 1,3-dihydroisobenzofurans (phthalans) containing functional substituents in the 1-position

Cited by 8 publications

References 3 publications

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Potentiality and Synthesis of O‐ and N‐Heterocycles: Pd‐Catalyzed Cyclocarbonylative Sonogashira Coupling as a Valuable Route to Phthalans, Isochromans, and Isoindolines

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

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Cyclization Reactions for the Synthesis of Phthalans and Isoindolines