Selective side-chain bromination of n-acyl-2,3-dialkylindoles: synthesis and chemical modification of pyrrolo[1,2-a]indoles

Vice, Susan F.; Copeland, Catherine R.; Forsey, Steven P.; Dmitrienko, Gary I.

doi:10.1016/s0040-4039(00)95008-1

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Cited by 20 publications

(1 citation statement)

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“…[ 2 ] Construction of polycyclic indoles usually requires multistep approaches. [ 3 ] The preparation of polyfunctional indoles is therefore an important research field. [ 4 ]…”

mentioning

confidence: 99%

Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis

Zhang

Shi

2012

ChemistryOpen

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“…[ 2 ] Construction of polycyclic indoles usually requires multistep approaches. [ 3 ] The preparation of polyfunctional indoles is therefore an important research field. [ 4 ]…”

mentioning

confidence: 99%

Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis

Zhang

Shi

2012

ChemistryOpen

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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A Novel One‐Pot, Two‐Step Synthesis of Polycyclic Indoles via Tandem Intramolecular Hydroamidation/Palladium‐Catalyzed Annulation

Liu

Zhang

et al. 2010

Adv Synth Catal

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Selective side-chain bromination of n-acyl-2,3-dialkylindoles: synthesis and chemical modification of pyrrolo[1,2-a]indoles

Cited by 20 publications

References 16 publications

Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis

Highly Stereoselective Synthesis of Polycyclic Indoles through Rearrangement/[4+2] Cycloaddition under Sequential Catalysis

The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

A Novel One‐Pot, Two‐Step Synthesis of Polycyclic Indoles via Tandem Intramolecular Hydroamidation/Palladium‐Catalyzed Annulation

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