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    Schiff and Mannich Reactions

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    Sat Montes
    The document summarizes the Schiff and Mannich reactions. The Schiff reaction is a reversible reaction that forms from the condensation of an aldehyde or ketone with a primary amine, producing a Schiff base. The Mannich reaction involves the amino alkylation of an acidic proton near a carbonyl group by formaldehyde and a primary or secondary amine, resulting in a beta-amino-carbonyl compound. Both reactions are important for organic synthesis and producing compounds with pharmacological activities.

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    Schiff and Mannich Reactions

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    Sat Montes
    64 views16 pages
    The document summarizes the Schiff and Mannich reactions. The Schiff reaction is a reversible reaction that forms from the condensation of an aldehyde or ketone with a primary amine, producing a Schiff base. The Mannich reaction involves the amino alkylation of an acidic proton near a carbonyl group by formaldehyde and a primary or secondary amine, resulting in a beta-amino-carbonyl compound. Both reactions are important for organic synthesis and producing compounds with pharmacological activities.

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    This document contains a brief presentation on Schiff and Mannich reactions.

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    The document summarizes the Schiff and Mannich reactions. The Schiff reaction is a reversible reaction that forms from the condensation of an aldehyde or ketone with a primary amine, producing a Schiff base. The Mannich reaction involves the amino alkylation of an acidic proton near a carbonyl group by formaldehyde and a primary or secondary amine, resulting in a beta-amino-carbonyl compound. Both reactions are important for organic synthesis and producing compounds with pharmacological activities.

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    © All Rights Reserved
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    64 views16 pages

    Schiff and Mannich Reactions

    Uploaded by

    Sat Montes
    The document summarizes the Schiff and Mannich reactions. The Schiff reaction is a reversible reaction that forms from the condensation of an aldehyde or ketone with a primary amine, producing a Schiff base. The Mannich reaction involves the amino alkylation of an acidic proton near a carbonyl group by formaldehyde and a primary or secondary amine, resulting in a beta-amino-carbonyl compound. Both reactions are important for organic synthesis and producing compounds with pharmacological activities.

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    of 16

    SCHIFF &

    MANNICH
    reactions
    BAMBICO, ISAIAH CERVERA, ALYZZA MIRANDA, ANDREA MONTES, SAT NANALI, EARL
    SCHIFF
    reaction
    reversible reaction that is usually formed due to the
    condensation of an aldehyde or ketone with primary amine

    Schiff Base
    nitrogen analog of an aldehyde or ketone in which C=O group
    is replaced by C=N-R group
    R may be an:
    aryl group (more stable and readily synthesized)
    alkyl group
    MANNICH
    reaction
    Organic reaction which consists of:
    amino alkylation of an acidic proton positioned next to
    a carbonyl functional group by formaldehyde alkyl
    group
    primary or secondary amine that results to beta-amino-
    carbonyl compound
    Also includes reactions between an aldimine and an alpha-
    methylene carbonyl (condensation reaction)
    SCHIFF
    mechanism REACTION
    STARTING MATERIALS

    primary or secondary ketone


    amine

    http://www.imedpub.com/articles/preparation-of-schiff-base-of-1-2-4triazole4amine-
    with3nitrobenzaldehyde-its-complexation-with-cu-ii-and-zn-ii-andantimicrobial-ac.php?aid=18885
    Imine Formation:
    SCHIFF
    mechanism REACTION
    1. Condensation of primary amines and active carbonyl groups by
    nucleophilic addition (formation of hemiaminal)
    2. Dehydration
    SCHIFF
    mechanism REACTION
    END PRODUCTS

    Schiff base water

    http://www.imedpub.com/articles/preparation-of-schiff-base-of-1-2-4triazole4amine-
    with3nitrobenzaldehyde-its-complexation-with-cu-ii-and-zn-ii-andantimicrobial-ac.php?aid=18885
    SCHIFF
    mechanism REACTION
    Imine Hydrolysis

    https://www.news-medical.net/life-sciences/Imine-Hydrolysis.aspx
    MANNICH
    mechanism REACTION
    STARTING MATERIALS

    (primary or) aldehyde carbonyl


    secondary amine compound

    https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry
    )/Reactions/Organic_Reactions/Mannich_Reaction
    MANNICH
    mechanism REACTION
    1. Formation of an iminium ion from the amine and the formaldehyde

    https://www.brainyresort.com/en/mannich-reaction/
    MANNICH
    mechanism REACTION
    2. Tautomerization of carbonyl group to enol

    https://www.brainyresort.com/en/mannich-reaction/
    MANNICH
    mechanism REACTION
    END PRODUCT

    β-amino-carbonyl or
    "Mannich Base"
    https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry
    )/Reactions/Organic_Reactions/Mannich_Reaction
    SCHIFF
    importance REACTION
    useful in terms of anti-inflammatory, analgesic,
    antimicrobial, anticonvulsant, antitubercular, anticancer,
    antioxidant, anthelmintic, antiglycation, and antidepressant
    activities
    serves as a catalyst, pigments and dyes, intermediates in
    organic synthesis, polymer stabilizers, and corrosion
    inhibitors
    MANNICH
    importance REACTION
    one of the most fundamental and important, C – C bond
    forming organic synthesis
    provides a reliable process for the aminocarbonyl
    preparation and a variety of other derivatives
    PRODUCTS FORMED
    Total synthesis of strychnine
    PRODUCTS FORMED
    Abbreviated biosynthesis of
    nicotine
    REFERENCES
    (n.d.). Retrieved from https://www.researchgate.net/figure/Mannich-reaction-with-tannins_fig13_272846512
    (n.d.). Retrieved from http://www1.biologie.uni-hamburg.de/b-
    online/library/newton/Chy251_253/Lectures/Mannich/MannichReactions.html
    Bruckner, R. (2010). Organic Mechanisms: Reactions, Stereochemistry, and Synthesis. Springer-Verlag. DOI: 10.1007/978-
    3-642-03651-4
    Dewick, P.M. (2006). Essentials of Organic Chemistry: For students of pharmacy, medicinal chemistry and biological
    chemistry. John Wiley & Sons.
    Dewick.(2009). Medicinal Natural Products A Biosynthetic Approach (3rd ed.). Antony Rowe Ltd, Chippenham, Wiltshire.
    Dewick, P.M. (2012). Medicinal natural products: a biosynthetic approach. 3e. John Wiley & Sons.
    Kajal, A., Bala, S., Kamboj, S., Sharma, N., & Saini, V. (2013). Schiff Bases: A Versatile Pharmacophore. Journal of
    Catalysts, 2013, 1–14. doi:10.1155/2013/893512
    Sani, U., Na’ibi, H. U., & Dailami, S. A. (2018). In vitro antimicrobial and antioxidant studies on N-(2- hydroxylbenzylidene)
    pyridine-2-amine and its M(II) complexes. Nigerian Journal of Basic and Applied Sciences, 25(1),
    81.doi:10.4314/njbas.v25i1.11
    Sari.(2014). The importance and applications of Schiff bases. 5th World Congress on Biotechnology. JBTBM an open access
    journal, 3(5), 1–238. doi: ISSN: 2155-952X Subramaniapillai, S. G. (2013). Mannich reaction: A versatile and convenient
    approach to bioactive skeletons. Journal of Chemical Sciences, 125(3), 467–482. doi: 10.1007/s12039-013-0405-y
    Xavier, A., Srividhya, N. (2014). Synthesis and Study of Schiff base Ligands. IOSR Journal of Applied Chemistry, 7(11), 06-
    15. doi: 10.9790/5736-071110615

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