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Literature DB >> 23957378

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

Abstract

Redox-neutral formation of C-P bonds inpan> the α-position of amines was achieved via a process that features a combination of an oxidative α-C-H bond functionalization and a reductive N-alkylation. Benzoic acid functions as an efficient catalyst in this three-component reaction of cyclic secondary amines, aldehydes and phosphine oxides to provide rapid access to α-amino phosphine oxides not easily accessible by classic Kabachnik-Fields reactions.

Entities: Chemical Disease Species

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Year: 2013 PMID： 23957378 PMCID： PMC3818705 DOI： 10.1021/ol401858k

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

53 in total

1. Product-selectivity control by the nature of the catalyst: Lewis acid-catalyzed selective formation of ring-fused tetrahydroquinolines and tetrahydroazepines via intramolecular redox reaction.

Authors: Guanghua Zhou; Junliang Zhang
Journal: Chem Commun (Camb) Date: 2010-08-10 Impact factor: 6.222

2. Alpha-amination of nitrogen heterocycles: ring-fused aminals.

Authors: Chen Zhang; Chandra Kanta De; Rudrajit Mal; Daniel Seidel
Journal: J Am Chem Soc Date: 2008-01-16 Impact factor: 15.419

3. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

Authors: Li Cui; Longwu Ye; Liming Zhang
Journal: Chem Commun (Camb) Date: 2010-03-30 Impact factor: 6.222

4. Direct α-functionalization of saturated cyclic amines.

Authors: Emily A Mitchell; Aldo Peschiulli; Nicolas Lefevre; Lieven Meerpoel; Bert U W Maes
Journal: Chemistry Date: 2012-07-24 Impact factor: 5.236

5. An efficient synthesis of a hydroxyethylamine (HEA) isostere and its α-aminophosphonate and phosphoramidate derivatives as potential anti-HIV agents.

Authors: Asish K Bhattacharya; Kalpeshkumar C Rana; Christophe Pannecouque; Eric De Clercq
Journal: ChemMedChem Date: 2012-07-11 Impact factor: 3.466

6. Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

Authors: Artur Mucha; Paweł Kafarski; Łukasz Berlicki
Journal: J Med Chem Date: 2011-08-05 Impact factor: 7.446

Review 7. Recent synthesis of aminophosphonic acids as potential biological importance.

Authors: Emilia D Naydenova; Petar T Todorov; Kolio D Troev
Journal: Amino Acids Date: 2009-02-20 Impact factor: 3.520

8. Highly efficient visible-light-induced aerobic oxidative C-C, C-P coupling from C-H bonds catalyzed by a gold(III)-complex.

Authors: Qicai Xue; Jin Xie; Hongming Jin; Yixiang Cheng; Chengjian Zhu
Journal: Org Biomol Chem Date: 2013-02-13 Impact factor: 3.876

9. Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

Authors: Sandip Murarka; Chen Zhang; Marlena D Konieczynska; Daniel Seidel
Journal: Org Lett Date: 2009-01-01 Impact factor: 6.005

10. Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

Authors: Chen Zhang; Daniel Seidel
Journal: J Am Chem Soc Date: 2010-02-17 Impact factor: 15.419

16 in total

1. 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

2. 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. Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.

Authors: Kempegowda Mantelingu; Yingfu Lin; Daniel Seidel
Journal: Org Lett Date: 2014-11-03 Impact factor: 6.005

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

1. Product-selectivity control by the nature of the catalyst: Lewis acid-catalyzed selective formation of ring-fused tetrahydroquinolines and tetrahydroazepines via intramolecular redox reaction.

2. Alpha-amination of nitrogen heterocycles: ring-fused aminals.

3. Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5 + 2] annulation.

4. Direct α-functionalization of saturated cyclic amines.

5. An efficient synthesis of a hydroxyethylamine (HEA) isostere and its α-aminophosphonate and phosphoramidate derivatives as potential anti-HIV agents.

6. Remarkable potential of the α-aminophosphonate/phosphinate structural motif in medicinal chemistry.

Review 7. Recent synthesis of aminophosphonic acids as potential biological importance.

8. Highly efficient visible-light-induced aerobic oxidative C-C, C-P coupling from C-H bonds catalyzed by a gold(III)-complex.

9. Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

10. Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

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

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

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

4. Redox-neutral α-arylation of amines.

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

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

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

8. Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

9. The redox-Mannich reaction.

10. Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.