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Research on Chemical Intermediates

, Volume 45, Issue 12, pp 5975–5987 | Cite as

An expeditious and green one-pot synthesis of 12-substituted-3,3-dimethyl-3,4,5,12-tetrahydrobenzo[b]acridine-1,6,11(2H)-triones

  • Saiedeh Kamalifar
  • Hamzeh KiyaniEmail author
Article
  • 69 Downloads

Abstract

In this study, several new 12-aryl/heteroaryl-3,3-dimethyl-tetrahydrobenzo[b]acridine-1,6,11(2H)-trione heterocyclic compounds that can be considered as 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones, have been synthesized through the three-component cyclocondensation of benzaldehydes/heteroaldehydes, 2-amino-1,4-naphthoquinone, and dimedone. The pot-, atom-, and step-economy reactions were implemented under reflux conditions. One of the most important aspects of this reaction is the use of ethanol as the reaction medium taking into account the principles of green chemistry. Not using a catalyst in this type of reactions is also significant from the standpoint of green chemistry. The protocol developed in this study has the benefits of the simplicity, no use of chromatographic methods for purification, structural diversity, employing non-toxic solvent, good-to-high yields, safety, and using cost-effective solvent. The structures of the newly synthesized 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones were confirmed employing spectroscopic data as well as elemental analysis.

Keywords

2-Amino-1,4-naphthoquinone Dimedone Green synthesis 12-Substituted-tetrahydrobenzo[b]acridine-1,6,11(2H)-trione Three-component cyclocondensation 

Notes

Acknowledgements

The authors are thankful to Damghan University Research Council for financial support of this study.

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© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.School of ChemistryDamghan UniversityDamghanIran

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