Synthesis of New 2-Vinylation Products of Indole via a Michael-Type Addition Reaction with Dimethyl Acetylenedicarboxylate and Their Diels−Alder Reactivity as Precursors of New Carbazoles

2006/09/01 by Hüseyin Çavdar, Nurullah Saraçoǧlu, Nurullah Saraçoğlu · 1 citation
Pharmacology, Toxicology and Pharmaceutics · Chemistry · #Bioactive Compounds and Antitumor Agents #Asymmetric Synthesis and Catalysis #Synthesis and Reactions of Organic Compounds

paper · doi:10.1021/jo061336f

Abstract

Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels-Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.

Cited by

• Cycloadditions of 4-Alkenyl-2-aminothiazoles with Nitroalkenes in the Formal Synthesis of Pramipexole: An Experimental and Computational Study. [europepmc]

Related

• Vinylindenes and some heteroanalogues in the Diels-Alder reaction. V. 3-Vinylindoles and quinones
• Double Palladium Catalyzed Reductive Cyclizations. Synthesis of 2,2′-, 2,3′-, and 3,3′-Bi-1H-indoles, Indolo[3,2-b]indoles, and Indolo[2,3-b]indoles
• Triflic Acid-Catalyzed Synthesis of Indole-Substituted Indane Derivatives via In Situ Formed Acetal-Facilitated Nucleophilic Addition and 4π-Electron-5-Carbon Electrocyclization Sequence
• Two-Step Route to Indoles and Analogues from Haloarenes: A Variation on the Fischer Indole Synthesis
• SYNTHESIS OF NEW 5-BROMO-1H-INDOLE-2,3-DIONE DERIVATIVES BY 1,3-DIPOLAR CYCLOADDITION