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Recent Advances in the Synthesis of Pyrroles - …

trifluoromethyl - pentafluorophenyl - vinylsulfone - Barton-Zard pyrrole synthesis - α-free pyrrole

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Barton–Zard reaction | Wiki | Everipedia

General procedure for the synthesis of pyrrole-2-carbonitriles 10a–j: A round bottomed flask equipped with a magnetic stir bar was charged with cyanopyrroline 6aj and DDQ (1.15–1.20 equiv) in toluene (15–20 mL/mmol 6). The reaction mixture was stirred under reflux until the starting material was consumed (TLC, 2–4 h). It was diluted with ethyl acetate and washed with 10% aqueous NaOH. The extracts were dried over MgSO4 and concentrated in vacuo to obtain the crude product which was purified by column chromatography.

General procedure for the synthesis of 2,4-disubstituted pyrroles 7a–i: A solution of cyanopyrroline 6ai in dichloromethane was transferred into a microwave reaction vessel. After removing the solvent in vacuo, the vessel was flushed with argon and closed with a cap. It was irradiated for 30 min (Pmax 180 W, pressure limit 7 bar, temperatures indicated in ) in a monomode microwave apparatus under air cooling. The pressurized vessel was opened very carefully inside a well-ventilated hood (caution, hydrogen cyanide!) and the residue was purified by column chromatography.

Barton–Zard reaction | Wikiwand

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between -methoxy--methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided -methoxy--methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between -methoxy--methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided -methoxy--methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.

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  • Barton-Zard Reaction - Chempedia - LookChem

    Barton–Zard synthesis, etc

  • Barton et al., Tetrahedron 46, 7587 (1990)

    3,4-dialkylpyrrole that is readily obtainable by Barton–Zard pyrrole synthesis

  • Helical chirality induction of expanded porphyrin analogues

    Barton-Zard Pyrrole Synthesis– C–3 is 1013 times more reactive to electrophilic attack than benzene23.

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