Literature DB >> 33562033

Synthesis of 2-Oxazolines from Ring Opening Isomerization of 3-Amido-2-Phenyl Azetidines.

Xin Zhou1, Baiyi Mao1, Zhanbin Zhang1.   

Abstract

Chiral 2-oxazolines are valuable building blocks and famous ligands for asymmetric catalysis. The most common synthesis involves the reaction of an amino alcohol with a carboxylic acid. In this paper, an efficient synthesis of 2-oxazolines has been achieved via the stereospecific isomerization of 3-amido-2-phenyl azetidines. The reactions were studied in the presence of both Brønsted and Lewis acids, and Cu(OTf)2 was found to be the most effective.

Entities:  

Keywords:  acid; amide; azetidine; isomerization; oxazoline

Mesh：

Substances：

Year:  2021        PMID： 33562033      PMCID： PMC7914936          DOI： 10.3390/molecules26040857

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  15 in total

1.  Synthesis of 2-Oxazolines by in Situ Desilylation and Cyclodehydration of β-Hydroxyamides.

Authors:  Marco Brandstätter; Fabian Roth; Nathan W Luedtke
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2.  A rational approach to the design of selective substrates and potent nontransportable inhibitors of the excitatory amino acid transporter EAAC1 (EAAT3). new glutamate and aspartate analogues as potential neuroprotective agents.

Authors:  G Campiani; M De Angelis; S Armaroli; C Fattorusso; B Catalanotti; A Ramunno; V Nacci; E Novellino; C Grewer; D Ionescu; T Rauen; R Griffiths; C Sinclair; E Fumagalli; T Mennini
Journal:  J Med Chem       Date:  2001-08-02       Impact factor: 7.446

3.  Synthesis and biological evaluation of 2-indolyloxazolines as a new class of tubulin polymerization inhibitors. Discovery of A-289099 as an orally active antitumor agent.

Authors:  Qun Li; Keith W Woods; Akiyo Claiborne; Stephen L Gwaltney; Kenneth J Barr; Gang Liu; Laura Gehrke; R Bruce Credo; Yu Hua Hui; Jang Lee; Robert B Warner; Peter Kovar; Michael A Nukkala; Nicolette A Zielinski; Stephen K Tahir; Michael Fitzgerald; Ki H Kim; Kennan Marsh; David Frost; Shi-Chung Ng; Saul Rosenberg; Hing L Sham
Journal:  Bioorg Med Chem Lett       Date:  2002-02-11       Impact factor: 2.823

4.  Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin via iridium-catalyzed asymmetric hydrogenation.

Authors:  Xiang-Yu Ye; Zhi-Qin Liang; Cong Jin; Qi-Wei Lang; Gen-Qiang Chen; Xumu Zhang
Journal:  Chem Commun (Camb)       Date:  2021-01-07       Impact factor: 6.222

5.  Open vessel mode microwave-assisted synthesis of 2-oxazolines from carboxylic acids.

Authors:  Rishi Sharma; Subramanian K Vadivel; Richard I Duclos; Alexandros Makriyannis
Journal:  Tetrahedron Lett       Date:  2009-10-21       Impact factor: 2.415

6.  Atroposelective Synthesis of Axially Chiral 3-Arylindoles by Copper-Catalyzed Asymmetric Cross-Coupling of Indoles with Quinones and Naphthoquinones.

Authors:  Chao-Chao Xi; Xiao-Jing Zhao; Jin-Miao Tian; Zhi-Min Chen; Kun Zhang; Fu-Min Zhang; Yong-Qiang Tu; Jia-Wei Dong
Journal:  Org Lett       Date:  2020-06-17       Impact factor: 6.005

7.  Synthesis, antimycobacterial and cytotoxic activity of α,β-unsaturated amides and 2,4-disubstituted oxazoline derivatives.

Authors:  Francisco G Avalos-Alanís; Eugenio Hernández-Fernández; Pilar Carranza-Rosales; Susana López-Cortina; Jorge Hernández-Fernández; Mario Ordóñez; Nancy E Guzmán-Delgado; Alejandro Morales-Vargas; Víctor M Velázquez-Moreno; María G Santiago-Mauricio
Journal:  Bioorg Med Chem Lett       Date:  2017-01-10       Impact factor: 2.823

8.  Modular synthesis of amine-functionalized oxazolines.

Authors:  Sridhar Rajaram; Matthew S Sigman
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

9.  The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions.

Authors:  Maria J Petersson; Ian D Jenkins; Wendy A Loughlin
Journal:  Org Biomol Chem       Date:  2008-12-18       Impact factor: 3.876

10.  A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products.

Authors:  Hai Huang; Wen Yang; Zuliang Chen; Zengwei Lai; Jianwei Sun
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825
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  1 in total

1.  Synthesis of tertiary alkyl fluorides and chlorides by site-selective nucleophilic ring-opening reaction of α-aryl azetidinium salts.

Authors:  Eiji Tayama; Kohei Kawai
Journal:  RSC Adv       Date:  2021-12-13       Impact factor: 3.361
  1 in total

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