17 research outputs found

    A mild and efficient method for the one-pot monocarboxymethylation of primary amines

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    A mild and efficient method for the monocarboxymethylation of primary amines that takes place under aq. conditions at room temp. is described. Treatment of an aq. soln. of a variety of primary amines with two equiv. of glyoxylic acid leads to the N-formyl glycine derivs. Direct hydrolysis of the crude reaction soln. leads to the products of amine monocarboxymethylation in good to excellent yield

    A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process

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    We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate <b>1</b> with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo­[1,2-<i>a</i>]­benzoxazinones <b>3</b> and pyrrolo­[1,2-<i>a</i>]­quinazolinones <b>4</b>, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of <b>1</b> followed by an intramolecular <i>N</i>,<i>O</i>-acetal- and <i>N</i>,<i>N</i>-aminal formation, respectively, which proceeds with good to excellent stereocontrol

    A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process

    No full text
    We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate <b>1</b> with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo­[1,2-<i>a</i>]­benzoxazinones <b>3</b> and pyrrolo­[1,2-<i>a</i>]­quinazolinones <b>4</b>, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of <b>1</b> followed by an intramolecular <i>N</i>,<i>O</i>-acetal- and <i>N</i>,<i>N</i>-aminal formation, respectively, which proceeds with good to excellent stereocontrol
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