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Literature DB >> 26785064

An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Abstract

Pyrrolidine and 1,2,3,4-tetrahydroisoquinoline (THIQ) undergo redox-neutral α-amidation with concurrent N-alkylation upon reaction with aromatic aldehydes and isocyanides. Reactions are promoted by acetic acid and represent a new variant of the Ugi reaction.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2016 PMID： 26785064 PMCID： PMC4934885 DOI： 10.1021/acs.orglett.5b03529

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

63 in total

1. 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

2. Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions.

Authors: Gaoxi Jiang; Jian Chen; Jie-Sheng Huang; Chi-Ming Che
Journal: Org Lett Date: 2009-10-15 Impact factor: 6.005

Review 3. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

4. Mild gold-catalyzed three-component dehydrogenative coupling of terminal alkynes to amines and indole-2-carboxaldehyde.

Authors: Jian Li; Hongni Wang; Jiangtao Sun; Yang Yang; Li Liu
Journal: Org Biomol Chem Date: 2014-04-28 Impact factor: 3.876

5. 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

6. 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

7. Asymmetric tandem 1,5-hydride shift/ring closure for the synthesis of chiral spirooxindole tetrahydroquinolines.

Authors: Weidi Cao; Xiaohua Liu; Jing Guo; Lili Lin; Xiaoming Feng
Journal: Chemistry Date: 2014-11-24 Impact factor: 5.236

8. 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

9. Organocatalytic C-H activation reactions.

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

10. The redox-Mannich reaction.

Authors: Weijie Chen; Daniel Seidel
Journal: Org Lett Date: 2014-05-23 Impact factor: 6.005

6 in total

1. Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Authors: Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal: Org Lett Date: 2018-01-12 Impact factor: 6.005

2. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors: Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal: Chemistry Date: 2016-11-09 Impact factor: 5.236