Literature DB >> 25575042

Synthesis of 4-quinolones via a carbonylative Sonogashira cross-coupling using molybdenum hexacarbonyl as a CO source.

Linda Åkerbladh1, Patrik Nordeman, Matyas Wejdemar, Luke R Odell, Mats Larhed.   

Abstract

A palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence for the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes via two different protocols is described. The first method (A) yields the cyclized products after only 20 min of microwave (MW) heating at 120 °C. The second method (B) is a gas-free one-pot two-step sequence which runs at room temperature, allowing the use of sensitive substituents (e.g., nitro and bromide groups). For both protocols, molybdenum hexacarbonyl was used as a solid source of CO.

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Year:  2015        PMID: 25575042     DOI: 10.1021/jo502400h

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization.

Authors:  Gang Cheng; Yingbei Qi; Xiaoqian Zhou; Rong Sheng; Yong-Zhou Hu; Youhong Hu
Journal:  Sci Rep       Date:  2017-06-30       Impact factor: 4.379

2.  Synthesis of unprotected glyco-alkynones via molybdenum-catalyzed carbonylative Sonogashira cross-coupling reaction.

Authors:  Mariana P Darbem; Henrique A Esteves; Robert A Burrow; Antônio A Soares-Paulino; Daniel C Pimenta; Hélio A Stefani
Journal:  RSC Adv       Date:  2022-01-13       Impact factor: 3.361

3.  Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade.

Authors:  Jurriën W Collet; Kelly Ackermans; Jeffrey Lambregts; Bert U W Maes; Romano V A Orru; Eelco Ruijter
Journal:  J Org Chem       Date:  2018-01-02       Impact factor: 4.354

4.  Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones.

Authors:  Naoki Kise; Yoshie Yoshimura; Tatsuhiro Manto; Toshihiko Sakurai
Journal:  ACS Omega       Date:  2019-11-15
  4 in total

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