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Literature DB >> 21247142

Redox isomerization via azomethine ylide intermediates: N-alkyl indoles from indolines and aldehydes.

Indubhusan Deb¹, Deepankar Das, Daniel Seidel.

Abstract

Indolines react with aromatic and heteroaromatic aldehydes to yield N-alkyl indoles in a benzoic acid catalyzed redox isomerization reaction. Azomethine ylides are intermediates in this process which was established by intramolecular [3 + 2] trapping experiments.

Entities: Chemical

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Year: 2011 PMID： 21247142 DOI： 10.1021/ol1031359

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

24 in total

1. The Redox-A³ Reaction.

Authors: Daniel Seidel
Journal: Org Chem Front Date: 2014-06-01 Impact factor: 5.281

2. 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

3. 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

4. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

Authors: YoungKu Kang; Matthew T Richers; Conrad H Sawicki; Daniel Seidel
Journal: Chem Commun (Camb) Date: 2015-07-07 Impact factor: 6.222

5. The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

Authors: Alena Yu Platonova; Daniel Seidel
Journal: Tetrahedron Lett Date: 2015-06 Impact factor: 2.415

10. 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

Redox isomerization via azomethine ylide intermediates: N-alkyl indoles from indolines and aldehydes.

1. The Redox-A³ Reaction.

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

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

4. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

5. The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

6. Redox-neutral α-arylation of amines.

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

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

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

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