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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1547 - 1551

DOI: https://doi.org/10.6023/cjoc1112301

Notes

Synthesis of Naphthylazuleno[2,1-d]pyrimidin-4-amines

  • Wang Daolin ,
  • Yu Jiayi ,
  • Li Wei ,
  • Cui Qingtao ,
  • Feng Shanshan
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  • Key Laboratory of Synthesis & Application of Functional Compound, College of Chemistry, Chemical Engineering & Food Safety, Bohai University, Jinzhou 121003

Received date: 2011-12-30

  Revised date: 2012-03-01

  Online published: 2012-04-11

Supported by

Project supported by the Science and Technology Department of Liaoning Province (No. 2011220022).

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Abstract

In this paper, a synthetic method for naphthylazuleno[2,1-d]pyrimidin-4-amines was reported, which began from cheap tropolone, ethyl naphthaleneacetate, malononitrile N,N-dimethylformamide dimethyl acetal (DMF-DMA) and anilines, followed by chlorination, condensation, cyclization and then Dimroth rearrangement reaction, to give naphthylazuleno[2,1-d]pyrimidin-4-amines in moderate yields. The structures of synthesized compounds were determined by 1H NMR, IR spectra and elemental analysis. This method provides several advantages such as good yield and simple work-up procedure.

Key words： azulene; azuleno[2,1-d]pyrimidine; ethyl naphthaleneacetate; DMF-DMA; aniline; synthesis

Cite this article

Wang Daolin , Yu Jiayi , Li Wei , Cui Qingtao , Feng Shanshan . Synthesis of Naphthylazuleno[2,1-d]pyrimidin-4-amines[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1547 -1551 . DOI: 10.6023/cjoc1112301

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