Iodine-Promoted One-pot Synthesis of Highly Substituted 4-Aminopyrroles and Bis-4-aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines

Hitesh B. Jalani, Jyotirling R. Mali, Hyejun Park, Jae Kyun Lee, Kiho Lee, Kyeong Lee, Yongseok Choi

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)

    Abstract

    An iodine-promoted one-pot synthesis of functionally diverse and highly substituted 4-aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in-situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4-aminopyrroles. This reaction involved the formation of two C−N bonds and one C−C bond by a formal [1+1+3] annulation approach. The present method provides an interesting framework of two 4-aminopyrrole units directly attached to a biphenyl core by the reaction of 4,4′-diacyl biphenyl, amine, and enamine groups. This Hantzsch-type one-pot reaction provides diverse 4-aminopyrroles, which could be useful in medicinal/material chemistry. (Figure presented.).

    Original languageEnglish
    Pages (from-to)4073-4079
    Number of pages7
    JournalAdvanced Synthesis and Catalysis
    Volume360
    Issue number21
    DOIs
    Publication statusPublished - 2018 Nov 5

    Bibliographical note

    Publisher Copyright:
    © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Keywords

    • 4-Aminopyrroles
    • Enamines
    • Hantzsch-type one-pot approach
    • Kornblum oxidation

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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