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Literature DB >> 22014326

A computational reinvestigation of the formation of N-alkylpyrroles via intermolecular redox amination.

Xiaosong Xue¹, Ao Yu, Yu Cai, Jin-Pei Cheng.

Abstract

A detailed mechanism of N-alkylpyrrole formation from 3-pyrroline and 2-phenylpropanal in the presence of a Brønsted acid catalyst was investigated in depth using the MP2 and DFT theories. The two mechanisms proposed earlier in recent literatures for this internal redox process were evaluated and were found not to account perfectly for the transition state and the energetic barrier of its formation. Based on the present calculations, a new mechanism was put forth.

Entities: Chemical Gene

Year: 2011 PMID： 22014326 DOI： 10.1021/ol2025247

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

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Cited

21 in total

1. Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors: Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal: Org Lett Date: 2020-01-27 Impact factor: 6.005

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-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors: Anirudra Paul; Alafate Adili; Daniel Seidel
Journal: Org Lett Date: 2019-03-06 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

A computational reinvestigation of the formation of N-alkylpyrroles via intermolecular redox amination.

1. Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

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-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

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

9. Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

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