The Ugly Duckling Metamorphosis: The Ammonia/Formaldehyde Couple Made Possible in Ugi Reactions.

    • Thaissa Pasquali F. Rosalbaa
    • Samia Sayegh A. Kasa
    • Ana Beatriz S. Sampaioa
    • Dr. Carlos Eduardo M. Salvadora
    • Dr. Carlos Kleber Z. Andradea
    • aInstituto de Química, Laboratório de Química Metodológica e Orgânica Sintética (LaQMOS), Universidade de Brasília, Campus Universitário, Asa Norte, 70904-970 Brasília, Brasil

    Ugi reactions are still a challenge when the concomitant use of ammonia and formaldehyde is required. Herein, we propose a strategy to overcome this challenge using hexamethylenetetramine (HMTA) as a singular key for the employment of these two simple starting materials in the Ugi reaction. Acylaminoacetamide derivatives were prepared in good to excellent yields by this new methodology. The scope and optimization of the reaction conditions were investigated. This novel methodology was successfully applied in the synthesis of two different diketopiperazines (DKPs) using the Ugi/Deprotection+Activation/Cyclization (UDAC) method. A continuous flow approach was also used in this methodology.

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