Fluorous Synthesis of Hydantoin‐, Piperazinedione‐, and Benzodiazepinedione‐Fused Tricyclic and Tetracyclic Ring Systems

Zhang, Wei; Lu, Yimin; Chen, Christine Hiu-Tung; Curran, Dennis P.; Geib, Steven J.

doi:10.1002/ejoc.200600077

Cited by 57 publications

(30 citation statements)

References 64 publications

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“…Scheme 31. Solution-phase syntheses of proline-fused heterocyclic systems by the microwave-assisted intermolecular 1,3-dipolar cycloaddition approach have been reported. [72][73][74] The one-pot three-component reactions of maleimide derivatives with the in situ generated azomethine ylides afford bicyclic prolines (e.g. 95) in good yields (Scheme 32).…”

Section: Cycloadditions Of Azomethine Ylidesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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The review describes the use of microwave technology to carry out 1,3-dipolar cycloaddition reactions, an important tool for the construction of five-membered heterocycles. Microwave methodology can be applied to generate 1,3-dipoles (nitrones, nitrile oxides, azomethine ylides, azomethine imines, nitrile imines, azides, carbonyl ylides) and to promote the subsequent cycloaddition and usually avoids harsh reaction conditions. This nonconventional energy source is able

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Section: Cycloadditions Of Azomethine Ylidesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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“…This reaction can be conducted under conventional or microwave heating. The cycloaddition was highly stereoselective and generated bicyclic pyrrolidines 19 [48]. The X-ray crystal structure analysis of compound 19 is shown in Fig.…”

Section: [3+2] Cycloaddition/de-tag/cyclization Protocolmentioning

confidence: 99%

“…14) [48]. Each of these three scaffolds has four stereocenters on the central pyrrolidine ring and up to four points of diversity (R 1 to R 4 ).…”

Section: [3+2] Cycloaddition/de-tag/cyclization Protocolmentioning

confidence: 99%

Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds

Zhang¹

2007

CCHTS

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Multicomponent reactions (MCRs) generate multiple bonds in a single reaction process, which is highly efficient to construct relatively complex molecules. Conducting post-MCR modification reactions further increases the molecular complexity and diversity. MCR has become a powerful approach to make drug-like molecules in lead generation chemistry. In fluorous MCR (F-MCR), one of the starting materials is attached to a fluorous tag and used as the limiting agent. After the MCR, the fluorous component is fished out from the reaction mixture and used for post-MCR modifications. The fluorous tag can be finally removed in traceless fashion by displacement or cyclization reactions. Unique fluorous technology such as fluorous solid-phase extraction (F-SPE) facilitates the separation process. Other techniques such as microwave irradiation and plate-to-plate SPE can also be used to make the F-MCR even more efficient. Syntheses of unique heterocyclic and natural product-like library scaffolds using Ugi/de-Boc/cyclization, MCR/Suzuki coupling, and [3+2] cycloaddition/detag/cyclization protocols are described in this paper.

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“…11 The reaction of 4 with a slight excess of phenylisocyanate in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP) afforded ureas 9. After F-SPE purification, compounds 9 were used for the microwave-assisted cyclization to cleave the fluorous linker and form hydantoinfused products 6.…”

mentioning

confidence: 99%

“…11 The reaction of 4a with chloroacetyl chloride afforded N-acylated products 10. The chloro group of 10 was displaced with BuNH 2 to afford 11.…”

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confidence: 99%

1,3-Dipolar Cycloaddition-based Synthesis of Diverse Heterocyclic Scaffolds

Zhang

2013

Chemistry Letters

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1,3-Dipolar cycloaddition reaction-based diversity-oriented synthesis developed from our research lab is highlighted. The initial [3 + 2] cycloaddition products are subjected to postcondensation modifications to afford heterocyclic scaffolds with substitutional, skeletal, and stereochemical variations. Multicomponent reactions and fluorous linker-facilitated separation are integrated to increase the efficiency of compound library synthesis.

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Fluorous Synthesis of Hydantoin‐, Piperazinedione‐, and Benzodiazepinedione‐Fused Tricyclic and Tetracyclic Ring Systems

Cited by 57 publications

References 64 publications

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Fluorous-Enhanced Multicomponent Reactions for Making Drug-Like Library Scaffolds

1,3-Dipolar Cycloaddition-based Synthesis of Diverse Heterocyclic Scaffolds

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