A Novel Synthesis of Isoindoline and Isoquinoline Using Chromium Carbene Complex

Mori, Miwako; Kuriyama, Kayoko; Ochifuji, Nagisa; Watanuki, Susumu

doi:10.1246/cl.1995.615

Cited by 17 publications

(4 citation statements)

References 6 publications

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“…In contrast, the development of efficient methods for the synthesis of substituted dihydroisoindoles seems to be a neglected area of research, and very few publications can be found in the literature . Common methods for the synthesis of 1,3-unsubstituted dihydroisoindoles are the metal-catalyzed − or base-induced [2 + 2 + 2] cocyclizations of bispropargylamines with alkynes. Another method employed an intramolecular Diels−Alder reaction to generate isoindolines with different N substituents .…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

2001

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The Pd-catalyzed intramolecular alpha-arylation of alpha-amino acid esters is described. Starting from readily available amino acids, the synthesis of a variety of isoindolines and tetrahydroisoquinoline carboxylic acid esters has been accomplished. Additionally, fused tricyclic systems can be efficiently prepared from cyclic amino acid esters. Reaction conditions have been found that allow the use of tert-butyl ester and N-(benzyloxycarbonyl) protecting groups.

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Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

2001

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“…The two-alkyne annulation provides for a synthesis of phenols starting with an alkyl carbene complex . This reaction can be effected either with 2 equiv of an alkyne in an intermolecular fashion or, more efficiently, with a diyne leading to an intramolecular process.…”

Section: Resultsmentioning

confidence: 99%

“…The penultimate product is a cyclohexadienone of the type 53 , which can be isolated under certain cases but most often is reduced to a phenol by chromium(0). A few cases are known in which this reaction has been carried out with unsymmetrical diynes, and in each case a single product has been reported and is that resulting from reaction of the terminal alkyne in preference to the internal alkyne . Neither the presence nor absence of the product resulting from the reaction of the internal alkyne is indicated in these reports.…”

Section: Resultsmentioning

confidence: 99%

Alkyne Competition in the Benzannulation Reaction with Chromium Carbene Complexes

Berbasov

Wulff

2010

J. Org. Chem.

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The benzannulation reaction of Fischer carbene complexes is investigated under conditions where the reaction of the carbene complex is occurring in the presence of two different alkynes. A series of competition experiments are examined where the effects of various structural factors are explored by pitting 10 different carbene complexes with 11 different alkynes. Terminal alkynes will react selectively over internal alkynes in all cases examined including both aryl and alkenyl complexes. Aryl carbene complexes with methoxy substituents do not give quite as high selectivity for terminal alkynes over internal alkynes (∼95:5) as do isopropoxy substituents (>99:1), whereas most alkenyl complexes give high selectivity with both substituents (>99:1). Competition experiments between two different terminal alkynes or between two different internal alkynes did not result in anything more than very modest selectivities at best (∼2:1). Excellent selectivities were realized between two different terminal acetylenes if one of the terminal acetylene was protected with a trimethylsilyl group. Finally, it was demonstrated that the high selectivities between terminal and internal alkynes can be utilized in the reaction with molecules that contain both types of alkyne functions.

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“…Finally, a different approach to isoindolines was described by Mori and co-workers. 146 The reaction between N,N-dipropargyl-4-toluenesulfonamides 167 and a chromium-carbene complex under a carbon monoxide atmosphere produced isoindolines 168 through a [2+2+1+1] cocyclization (Scheme 64). The experimental reaction conditions were optimized for N,N-dipropargyl-4toluenesulfonamide (167, R = H) and then extended to internal diynes which generated isoindolines 168 having three substituents on the aromatic ring in good yields.…”

Section: Scheme 63 [2+2+2] Cycloaddition Of Nn-dipropargyl-4-toluenementioning

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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A Novel Synthesis of Isoindoline and Isoquinoline Using Chromium Carbene Complex

Cited by 17 publications

References 6 publications

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

Alkyne Competition in the Benzannulation Reaction with Chromium Carbene Complexes

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines

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A Novel Synthesis of Isoindoline and Isoquinoline Using Chromium Carbene Complex

Cited by 17 publications

References 6 publications

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid Esters

Alkyne Competition in the Benzannulation Reaction with Chromium Carbene Complexes

Cyclization Reactions for the Synthesis of Phthalans and Isoindolines­

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Cyclization Reactions for the Synthesis of Phthalans and Isoindolines