Convenient preparation of amino acid derivatives with two 13C labels

Fornicola, Richard S.; Montgomery, John

doi:10.1016/s0040-4039(99)01783-9

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Aldehydes With Nitro Compounds1

Nitroaldol Reaction On Indolyl-3-carbaldehydes1

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2003

2024

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Cited by 8 publications

(2 citation statements)

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“…Substituted nitro acrylic esters 11 37 have been reported 38,39 while a general preparative procedure has been described starting from aldehydes and ethyl nitroacetate catalysed by TiCl 4 and amine. 40,41…”

Section: Aldehydes With Nitro Compoundsmentioning

confidence: 99%

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

De Sarlo,

Machetti

2023

Org. Biomol. Chem.

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Section: Aldehydes With Nitro Compoundsmentioning

confidence: 99%

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

De Sarlo,

Machetti

2023

Org. Biomol. Chem.

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“…Condensation of 3-formylindole 120 with excess of methyl nitroacetate is best performed in the presence of TiCl 4 and NMO and the obtained nitroalkene 121 can be made to react with different organometallic reagents leading to substituted nitro indoles 122 in good to satisfactory yields. (Scheme ). , This procedure also allows the introduction in compounds 122 of labeled atoms using 13 C methyl nitroacetate for the preparation of compounds 121 …”

Section: Nitroaldol Reaction On Indolyl-3-carbaldehydesmentioning

confidence: 99%

Synthetic Approaches to 3-(2-Nitroalkyl) Indoles and Their Use to Access Tryptamines and Related Bioactive Compounds

2014

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Introduction 7108 2. Reaction of Indoles with Nitroalkenes 7109 2.1. Uncatalyzed FC Reactions 7109 2.2. Brønsted Acid Catalyzed FC Reactions 7110 2.3. Lewis Acid Catalyzed FC Reactions 7112 2.4. Organocatalyzed FC Reactions 7117 2.5. FC Reactions Included in Tandem, Cascade, and One-Pot Processes 7119 2.6. Base Promoted Conjugate Additions of Indoles to Nitroalkenes 7123 3. Reaction of Indolenine Derivatives 7124 3.1. Reaction of Nitroalkanes with Gramines 7124 3.2. Reaction of Nitroalkanes with Sulfonyl Indoles 7124 3.3. Reaction of Nitroalkanes with Other Derivatives 7126 4. Nitroaldol Reaction on Indolyl-3-carbaldehydes 7126 5. Direct Synthesis of Nitro Indoles by the Fischer Reaction 7129 6. Synthetic Applications of Nitro Indoles 7129 6.1. Synthesis of Tryptophans 7129 6.2. Synthesis of Polycyclic Compounds 7130 6.2.1. Ergot Alkaloids and Related Derivatives 7130 6.2.2. Other Polycyclic Compounds 7132 6.3. Synthesis of β-Carbolines 7135 6.4. Synthesis of Other Tryptamine Derivatives 7141 7. Conclusion 7143 Author Information 7143 Corresponding Author 7143 Notes 7143 Biographies 7143 Acknowledgments 7144 Abbreviations 7144 References 7144

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An Efficient Synthetic Method to Nonnatural α‐ and β‐Tryptophan Analogues via Friedel‐Crafts Alkylation of Indoles with Nitroacrylates

Sui¹,

Liu²,

Wang³

et al. 2007

Chin. J. Chem.

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Convenient preparation of amino acid derivatives with two 13C labels

Cited by 8 publications

References 30 publications

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

Synthetic Approaches to 3-(2-Nitroalkyl) Indoles and Their Use to Access Tryptamines and Related Bioactive Compounds

An Efficient Synthetic Method to Nonnatural α‐ and β‐Tryptophan Analogues via Friedel‐Crafts Alkylation of Indoles with Nitroacrylates

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