Literature DB >> 33399609

Intramolecular N-Me and N-H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles.

Mahesh P Paudyal1, Mingliang Wang2, Juha H Siitonen3, Yimin Hu4, Muhammed Yousufuddin5, Hong C Shen4, John R Falck1, László Kürti3.   

Abstract

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.

Entities:  

Mesh：

Substances：

Year:  2021        PMID： 33399609      PMCID： PMC8183519          DOI： 10.1039/d0ob02122a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  13 in total

1.  Discovery and Rational Design of Natural-Product-Derived 2-Phenyl-3,4-dihydro-2H-benzo[f]chromen-3-amine Analogs as Novel and Potent Dipeptidyl Peptidase 4 (DPP-4) Inhibitors for the Treatment of Type 2 Diabetes.

Authors:  Shiliang Li; Hongling Xu; Shichao Cui; Fangshu Wu; Youli Zhang; Mingbo Su; Yinghui Gong; Shaobing Qiu; Qian Jiao; Chun Qin; Jiwei Shan; Ming Zhang; Jiawei Wang; Qiao Yin; Minghao Xu; Xiaofeng Liu; Rui Wang; Lili Zhu; Jia Li; Yufang Xu; Hualiang Jiang; Zhenjiang Zhao; Jingya Li; Honglin Li
Journal:  J Med Chem       Date:  2016-07-19       Impact factor: 7.446

2.  Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids.

Authors:  Zhiwei Ma; Zhe Zhou; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

3.  Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins.

Authors:  Jawahar L Jat; Mahesh P Paudyal; Hongyin Gao; Qing-Long Xu; Muhammed Yousufuddin; Deepa Devarajan; Daniel H Ess; László Kürti; John R Falck
Journal:  Science       Date:  2014-01-03       Impact factor: 47.728

4.  Lewis acid catalyzed S(N)2-type ring opening of N-activated aziridines with electron-rich arenes/heteroarenes.

Authors:  Manas K Ghorai; Deo Prakash Tiwari; Nikita Jain
Journal:  J Org Chem       Date:  2013-07-09       Impact factor: 4.354

5.  Access to Aminated Saturated Oxygen Heterocycles via Copper-Catalyzed Aminooxygenation of Alkenes.

Authors:  Jian Xie; Yue-Wei Wang; Lian-Wen Qi; Bo Zhang
Journal:  Org Lett       Date:  2017-02-16       Impact factor: 6.005

6.  Studies on orchidaceae alkaloids. XXXII. Crepidine, crepidamine and dendrocrepine, three alkaloids from Dendrobium crepidatum Lindl.

Authors:  M Elander; K Leander; J Rosenblom; E Ruusa
Journal:  Acta Chem Scand       Date:  1973

7.  Catalytic intermolecular alkene oxyamination with nitrenes.

Authors:  Geoffroy Dequirez; Jennifer Ciesielski; Pascal Retailleau; Philippe Dauban
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

8.  Towards the discovery of drug-like epigallocatechin gallate analogs as Hsp90 inhibitors.

Authors:  Rohit Bhat; Amna T Adam; Jungeun Jasmine Lee; Thomas A Gasiewicz; Ellen C Henry; David P Rotella
Journal:  Bioorg Med Chem Lett       Date:  2014-04-04       Impact factor: 2.823

9.  Synthesis and catalytic application of chiral 1,1'-Bi-2-naphthol- and biphenanthrol-based pincer complexes: selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate.

Authors:  Juhanes Aydin; K Senthil Kumar; Mahmoud J Sayah; Olov A Wallner; Kálmán J Szabó
Journal:  J Org Chem       Date:  2007-05-25       Impact factor: 4.354

10.  Omarigliptin (MK-3102): a novel long-acting DPP-4 inhibitor for once-weekly treatment of type 2 diabetes.

Authors:  Tesfaye Biftu; Ranabir Sinha-Roy; Ping Chen; Xiaoxia Qian; Dennis Feng; Jeffrey T Kuethe; Giovanna Scapin; Ying Duo Gao; Youwei Yan; Davida Krueger; Annette Bak; George Eiermann; Jiafang He; Jason Cox; Jacqueline Hicks; Kathy Lyons; Huaibing He; Gino Salituro; Sharon Tong; Sangita Patel; George Doss; Aleksandr Petrov; Joseph Wu; Shiyao Sherrie Xu; Charles Sewall; Xiaoping Zhang; Bei Zhang; Nancy A Thornberry; Ann E Weber
Journal:  J Med Chem       Date:  2014-04-02       Impact factor: 7.446
View more
  1 in total

1.  The Evaluation of DHPMs as Biotoxic Agents on Pathogen Bacterial Membranes.

Authors:  Barbara Gawdzik; Paweł Kowalczyk; Dominik Koszelewski; Anna Brodzka; Joanna Masternak; Karol Kramkowski; Aleksandra Wypych; Ryszard Ostaszewski
Journal:  Membranes (Basel)       Date:  2022-02-18
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.