Synthesis of indolyloxypropanolamines bearing the 2-(1H-indol-3yl)-1,1-dimethylethyl group: structure—activity studies and anti-hypertensive activity

Wagnon, Jean; Plouzané, Claude; Tonnerre, Bernard; Demarne, H.; Serre, M; Lacour, Colette; Gougat, J.; Gagnol, J. P.; Gautier, Patrick

doi:10.1016/0223-5234(88)90161-4

Cited by 2 publications

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“…Indole analogues of labetalol, a known antihypertensive drug, can be prepared by reaction of suitable tryptamine derivatives 325 with epoxides 326 (Scheme ). , The required tryptamines 325 are obtained by reaction of gramines 324 with excess of 2-nitropropane in the presence of KOH followed by reduction of the intermediate nitro indoles with hydrazine hydrate/Nickel-Raney. The regioselective ring-opening of epoxides 326 to the final amino alcohol derivatives 327 is efficiently carried out under solvent-free conditions, although ethanol at reflux can also be be used as a solvent.…”

Section: Synthetic Applications Of Nitro Indolesmentioning

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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Section: Synthetic Applications Of Nitro Indolesmentioning

confidence: 99%