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Literature DB >> 35100511

Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.

Anirudra Paul¹, Camille Vasseur¹, Scott D Daniel¹, Daniel Seidel¹.

Abstract

Relatively unstable cyclic imines, generated in situ from their corresponding alicyclic amines via oxidation of their lithium amides with simple ketone oxidants, engage aryllithium compounds containing a leaving group on an ortho-methylene functionality to provide polycyclic isoindolines in a single operation. The scope of this transformation includes pyrrolidine, piperidine, azepane, azocane, and piperazines.

Entities: Chemical

Year: 2022 PMID： 35100511 PMCID： PMC9039734 DOI： 10.1021/acs.orglett.2c00018

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.072

56 in total

1. Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

Authors: Qin Zang; Salim Javed; Patrick Porubsky; Farman Ullah; Benjamin Neuenswander; Gerald H Lushington; Fatima Z Basha; Michael G Organ; Paul R Hanson
Journal: ACS Comb Sci Date: 2012-02-06 Impact factor: 3.784

2. Ruthenium-Catalyzed Hydrogen Evolution o-Aminoalkylation of Phenols with Cyclic Amines.

Authors: Liang Cao; He Zhao; Zhenda Tan; Rongqing Guan; Huanfeng Jiang; Min Zhang
Journal: Org Lett Date: 2020-06-03 Impact factor: 6.005

Review 3. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors: Edon Vitaku; David T Smith; Jon T Njardarson
Journal: J Med Chem Date: 2014-10-07 Impact factor: 7.446

4. Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α-Arylated Amines and N-Heterocycles.

Authors: Ana Koperniku; Laurel L Schafer
Journal: Chemistry Date: 2021-03-04 Impact factor: 5.236

5. Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates.

Authors: Alexandre F Trindade; Emily L Faulkner; Andrew G Leach; Adam Nelson; Stephen P Marsden
Journal: Chem Commun (Camb) Date: 2020-07-06 Impact factor: 6.222

6. Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C₆F₅)₃ and a Chiral Lewis Acid Co-Catalyst.

Authors: Yejin Chang; Min Cao; Jessica Z Chan; Cunyuan Zhao; Yuankai Wang; Rose Yang; Masayuki Wasa
Journal: J Am Chem Soc Date: 2021-01-29 Impact factor: 15.419

7. 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

Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.

1. Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.

2. Ruthenium-Catalyzed Hydrogen Evolution o-Aminoalkylation of Phenols with Cyclic Amines.

Review 3. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

4. Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α-Arylated Amines and N-Heterocycles.

5. Fragment-oriented synthesis: β-elaboration of cyclic amine fragments using enecarbamates as platform intermediates.

6. Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C₆F₅)₃ and a Chiral Lewis Acid Co-Catalyst.

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

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

9. A cascade reaction with iminium ion isomerization as the key step leading to tetrahydropyrimido[4,5-d]pyrimidines.

10. Asymmetric Redox-Annulation of Cyclic Amines.

1. Regioselective α-Cyanation of Unprotected Alicyclic Amines.