Literature DB >> 16901148

Skraup-Doebner-Von Miller quinoline synthesis revisited: reversal of the regiochemistry for gamma-aryl-beta,gamma-unsaturated alpha-ketoesters.

Yan-Chao Wu1, Li Liu, Hui-Jing Li, Dong Wang, Yong-Jun Chen.   

Abstract

A reversal of the standard regiochemistry of the Skraup-Doebner-Von Miller quinoline synthesis was observed when anilines were condensed with gamma-aryl-beta,gamma-unsaturated alpha-ketoesters in refluxing TFA. The reaction is proposed to involve 1,2-addition of the anilines to gamma-aryl-beta,gamma-unsaturated alpha-ketoesters to form Schiff's base adducts, followed by cyclization and oxidation. The products were unambiguously shown to the 2-carboxy-4-arylquinolines by spectroscopy and X-ray crystallographic analysis.

Entities:  

Year:  2006        PMID： 16901148     DOI： 10.1021/jo060290n

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


  7 in total

1.  Facile Synthesis and Photophysical Characterization of New Quinoline Dyes.

Authors:  Giovanny Carvalho Dos Santos; Aloisio de Andrade Bartolomeu; Valdecir Farias Ximenes; Luiz Carlos da Silva-Filho
Journal:  J Fluoresc       Date:  2016-10-27       Impact factor: 2.217

Review 2.  Recent advances in chemistry and therapeutic potential of functionalized quinoline motifs - a review.

Authors:  Olayinka O Ajani; King T Iyaye; Olabisi T Ademosun
Journal:  RSC Adv       Date:  2022-06-24       Impact factor: 4.036

3.  Synthesis and fluorescence properties of 5,7-diphenylquinoline and 2,5,7-triphenylquinoline derived from m-terphenylamine.

Authors:  Shujian Qi; Kehui Shi; Hongyin Gao; Qiancai Liu; Hong Wang
Journal:  Molecules       Date:  2007-05-12       Impact factor: 4.411

4.  (E)-1-(6-Chloro-2-methyl-4-phenyl-3-quinol-yl)-3-(4-ethoxy-phen-yl)prop-2-en-1-one.

Authors:  Tara Shahani; Hoong-Kun Fun; S Sarveswari; V Vijayakumar; R Venkat Ragavan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-16

5.  Efficient construction of pyrazolo[1,5-a]pyrimidine scaffold and its exploration as a new heterocyclic fluorescent platform.

Authors:  Yan-Chao Wu; Hui-Jing Li; Li Liu; Dong Wang; Hua-Zheng Yang; Yong-Jun Chen
Journal:  J Fluoresc       Date:  2007-11-16       Impact factor: 2.217

6.  One-pot phosphine-catalyzed syntheses of quinolines.

Authors:  San Khong; Ohyun Kwon
Journal:  J Org Chem       Date:  2012-09-06       Impact factor: 4.354

7.  Methyl 5-hy-droxy-3-phenyl-1,2-oxazolidine-5-carboxyl-ate.

Authors:  Jia Ye; Ya-Nan Liu; Yu Cheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-25
  7 in total

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