ArticleOrganic letters2014
A practical route to substituted 7-aminoindoles from pyrrole-3-carboxaldehydes.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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8 citing papers in PubMed.
- A rapid, metal-free synthesis of amino- and hydroxyphenanthrenes with tunable photophysical properties.RSC advances · 2025Article
- β‑Selective Addition of Pyrroles to Electron-Deficient Alkenes in Both Catalytic and Stoichiometric Modes on B(CACS omega · 2025Article
- Silylpyrrole Oxidation En Route to Saxitoxin Congeners Including 11-Saxitoxinethanoic Acid.The Journal of organic chemistry · 2021Article
- Cyanoamidine Cyclization Approach to Remdesivir's Nucleobase.Organic letters · 2020Article
- Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties.International journal of molecular sciences · 2018Article
- Synthesis and Evaluation of N-(3-Trifluoroacetyl-indol-7-yl) Acetamides for Potential In Vitro Antiplasmodial Properties.Molecules (Basel, Switzerland) · 2017Article
- Unusual Blue-Shifted Acid-Responsive Photoluminescence Behavior in 6-Amino-8-cyanobenzo[1,2-RSC advances · 2016Article
- One-pot synthesis of highly substituted N-fused heteroaromatic bicycles from azole aldehydes.Organic letters · 2015Article
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Abstract
Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile for facile intramolecular Hoeben-Hoesch reaction in the presence of BF3·OEt2. Syntheses of 2,5- and 3,5-disubstituted 7-aminoindoles are illustrated. Additionally, dianion alkylation of the allylic nitrile is demonstrated to furnish, after cyclization, 5,6-disubstituted 7-aminoindoles to further exemplify this scalable and high-yielding method.
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