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Literature DB >> 21280625

Redox-neutral indole annulation cascades.

Michael C Haibach¹, Indubhusan Deb, Chandra Kanta De, Daniel Seidel.

Abstract

Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.

Entities: Chemical

Mesh：

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Year: 2011 PMID： 21280625 DOI： 10.1021/ja110713k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

19 in total

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors: Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal: Synthesis (Stuttg) Date: 2013-10-06 Impact factor: 3.157

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors: Deepankar Das; Daniel Seidel
Journal: Org Lett Date: 2013-08-19 Impact factor: 6.005

3. C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors: Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal: J Org Chem Date: 2012-06-06 Impact factor: 4.354

9. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors: Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal: J Org Chem Date: 2013-04-02 Impact factor: 4.354

10. Organocatalytic C-H activation reactions.

Authors: Subhas Chandra Pan
Journal: Beilstein J Org Chem Date: 2012-08-27 Impact factor: 2.883

Redox-neutral indole annulation cascades.

1. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

2. Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

3. C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

4. Condensation-Based Methods for the C-H Bond Functionalization of Amines.

5. Redox-neutral α-arylation of amines.

6. Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

7. Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

8. Redox-neutral α,β-difunctionalization of cyclic amines.

9. Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

10. Organocatalytic C-H activation reactions.