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Literature DB >> 27623988

Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions.

Lan-Gui Xie¹, Saad Shaaban¹, Xiangyu Chen¹, Nuno Maulide².

Abstract

The synthesis of pyridines through direct intermolecular cycloaddition of alkynes and nitriles is a contemporary challenge in organic synthesis. A Brønsted acid mediated formal [2+2+2] cycloaddition of heteroalkynes and nitriles was developed that proceeds under mild conditions. This constitutes a modular approach to highly substituted pyridine cores.

Entities: Chemical

Keywords: alkynes; cycloaddition; heteroalkynes; nitriles; pyridines

Year: 2016 PMID： 27623988 DOI： 10.1002/anie.201606604

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

7 in total

1. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors: Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal: Org Lett Date: 2017-07-13 Impact factor: 6.005

2. Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates.

Authors: Miran Lemmerer; Christopher J Teskey; Daniel Kaiser; Nuno Maulide
Journal: Monatsh Chem Date: 2017-11-28 Impact factor: 1.451

3. Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors: Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal: Angew Chem Int Ed Engl Date: 2017-09-19 Impact factor: 15.336

4. Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates.

Authors: Jinlong Qian; Jinlong Zhang; Huameng Yang; Lei Kang; Gaoxi Jiang
Journal: Chem Sci Date: 2019-08-07 Impact factor: 9.825

Metal-Free Synthesis of Highly Substituted Pyridines by Formal [2+2+2] Cycloaddition under Mild Conditions.

1. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

2. Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates.

3. Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

4. Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates.

5. One-step synthesis of benzo[b]thiophenes by aryne reaction with alkynyl sulfides.

6. Fine-tuned organic photoredox catalysts for fragmentation-alkynylation cascades of cyclic oxime ethers.

7. On the formation of seven-membered rings by arene-ynamide cyclization.