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Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones.
J Org Chem. 2014 Jun 20; 79(12):5781-6.JO

Abstract

The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds at room temperature, under p-TsOH catalysis, affords substituted polycyclic aromatic indene derivatives through a domino reaction involving the formation of a cationic allenylium intermediate. This species can undergo a series of competitive intramolecular cascade reactions, leading to a conjugated inden-2-one. This simple method allows the efficient synthesis of substituted indenes and inden-2-ones, in two steps, from aromatic ketones.

Authors+Show Affiliations

Centro de Quı́mica-Vila Real, Universidade de Trás-os-Montes e Alto Douro , 5000-801 Vila Real, Portugal.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24846324

Citation

Sousa, Céu M., et al. "Acid-catalyzed Domino Reactions of Tetraarylbut-2-yne-1,4-diols. Synthesis of Conjugated Indenes and Inden-2-ones." The Journal of Organic Chemistry, vol. 79, no. 12, 2014, pp. 5781-6.
Sousa CM, Berthet J, Delbaere S, et al. Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones. J Org Chem. 2014;79(12):5781-6.
Sousa, C. M., Berthet, J., Delbaere, S., & Coelho, P. J. (2014). Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones. The Journal of Organic Chemistry, 79(12), 5781-6. https://doi.org/10.1021/jo500907z
Sousa CM, et al. Acid-catalyzed Domino Reactions of Tetraarylbut-2-yne-1,4-diols. Synthesis of Conjugated Indenes and Inden-2-ones. J Org Chem. 2014 Jun 20;79(12):5781-6. PubMed PMID: 24846324.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Acid-catalyzed domino reactions of tetraarylbut-2-yne-1,4-diols. Synthesis of conjugated indenes and inden-2-ones. AU - Sousa,Céu M, AU - Berthet,Jerome, AU - Delbaere,Stephanie, AU - Coelho,Paulo J, Y1 - 2014/05/30/ PY - 2014/5/22/entrez PY - 2014/5/23/pubmed PY - 2014/12/18/medline SP - 5781 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 79 IS - 12 N2 - The reaction of tetraarylbut-2-yne-1,4-diols with electron-rich aromatic compounds at room temperature, under p-TsOH catalysis, affords substituted polycyclic aromatic indene derivatives through a domino reaction involving the formation of a cationic allenylium intermediate. This species can undergo a series of competitive intramolecular cascade reactions, leading to a conjugated inden-2-one. This simple method allows the efficient synthesis of substituted indenes and inden-2-ones, in two steps, from aromatic ketones. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/24846324/Acid_catalyzed_domino_reactions_of_tetraarylbut_2_yne_14_diols__Synthesis_of_conjugated_indenes_and_inden_2_ones_ L2 - https://doi.org/10.1021/jo500907z DB - PRIME DP - Unbound Medicine ER -