Literature DB >> 11397153

A general preparation of pyridines and pyridones via the annulation of ketones and esters.

J F Marcoux1, F A Marcotte, J Wu, P G Dormer, I W Davies, D Hughes, P J Reider.   

Abstract

A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the beta-position. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

Entities:  

Year:  2001        PMID: 11397153     DOI: 10.1021/jo0155198

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


  2 in total

1.  Synthesis of new allylidene amino phenol-containing Schiff bases and metal complex formation using trimethinium salts.

Authors:  Ziba Rafiee Samani; Abdolmohammad Mehranpour
Journal:  RSC Adv       Date:  2021-06-18       Impact factor: 4.036

2.  BF3·Et2O-Mediated annulation of α-keto acids with aliphatic ketones for the synthesis of γ-hydroxy-butenolides and γ-alkylidene-butenolides.

Authors:  Zhenfeng Cheng; Qingyun Gu; Yushan Xie; Yanan Zhang; Xiaobao Zeng
Journal:  RSC Adv       Date:  2022-08-25       Impact factor: 4.036

  2 in total

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