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A mechanistic insight into the acid catalyzed, one-pot synthesis of isoindole-fused quinazolin 4-ones

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Abstract

One-pot synthesis of isoindole fused quinazolin 4-ones via intramolecular 1,3 hydride transfer in the presence of acid catalyst has been described. Substrate scope and mechanistic insights were investigated. Substituents on the amide side have a negligible influence on the key step and therefore the method have wide scope for accessing various bicyclic core structure.

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A Mechanistic Insight into the Acid Catalyzed, One-Pot Synthesis of Isoindole-Fused Quinazolin 4-ones

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References

  1. Nesměrák K, Pelouchová H, Všetečka V, Němec I and Gabriel J 1998 Antifungal effects of new heterocyclic compounds, 6H-pyrimido[2,1-a]isoindole derivatives Folia Microbiol. 43 39

    Article  Google Scholar 

  2. Troschütz R and Heinemann O 1995 On the Fluorescence Reaction of Pharmaceutically Important o-Aminobenzamides and o-Aminobenzenesulfonamides with Phthalaldehyde and Analogues Arch. Pharm. 328 759

    Article  Google Scholar 

  3. Radfar I, Miraki M K, Ghandi L, Esfandiary N, Abbasi S, Karimi M and Heydari A 2018 BF3-Grafted Fe3O4@sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of dihydroquinazolinones (DHQZs) and bis 3-indolyl methanes (BIMs) Appl. Organomet. Chem. 32 e4431

    Article  Google Scholar 

  4. Ghorbani-Choghamarani A and Norouzi M 2014 Synthesis of copper (II)-supported magnetic nanoparticle and study of its catalytic activity for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones J. Mol. Catal. A 395 172

    Article  CAS  Google Scholar 

  5. Mhaske S B and Argade N P 2006 The chemistry of recently isolated naturally occurring quinazolinone alkaloids Tetrahedron 62 9787

    Article  CAS  Google Scholar 

  6. Sun X, Hu Y, Nie S-z, Yan Y-y, Zhang X-j and Yan M 2013 Efficient construction of C=N double bonds via acceptorless dehydrogenative coupling Adv. Synth. Catal. 355 2179

    Article  CAS  Google Scholar 

  7. Bakavoli M, Davoodni A, Rahimizadeh M and Heravi M M 2006 Synthesis of dibenzo[b,g][1,5]diazoninedione and isoindolo[2,1-a]quinazoline derivatives Mendeleev Commun. 16 29

  8. Kovtunenko V A, Fal’kovskaya O T, Tyltin A K and Babichev F S 1986 11-H-isoindolo[1,2-c][1,2,4]benzothiadiazine-5,5-dioxides Ukr. Khim. Zh. 52 213

  9. Abdel-Latif F, El-Shaieb K and El-Deen A G 2011 An efficient and simple route to prospective biologically active isoindoloquinazoline, pyrimidineand thiazine derivatives using 2-amino-N’-arylbenzamidine and related compounds as starting materials Z. Naturforsch. 66b 965

  10. Ukhin L Y, Kuzrmina L G, Gribanova T N, Belousova L V and Orlova Z I 2009 Synthesis and properties of a new fused heterocyclic system 12H-benzo[5,6][1,2,4]triazepino[3,4-a]isoindol-5(6H)-one Russ. Chem. Bull., Int. Ed. 57 186

  11. Wang L and Xiao J 2016 Hydrogen-Atom Transfer Reactions Top. Curr. Chem. 374 17

    Article  Google Scholar 

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Acknowledgements

Authors are thankful to the SERB New Delhi, (EMR/2014/000542) and Jadavpur University, Kolkata for financial support. Special thanks to Dr. P. Mahata, Department of Chemistry, JU for his kind support for solving crystal structure.

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Authors and Affiliations

  1. Department of Chemistry, Jadavpur University, Kolkata, 700 032, West Bengal, India

    Mohabul A Mondal, Sudipta Mondal & Abdul A Khan

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  1. Mohabul A Mondal
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  2. Sudipta Mondal
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  3. Abdul A Khan
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Correspondence to Mohabul A Mondal.

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Mondal, M.A., Mondal, S. & Khan, A.A. A mechanistic insight into the acid catalyzed, one-pot synthesis of isoindole-fused quinazolin 4-ones. J Chem Sci 132, 63 (2020). https://doi.org/10.1007/s12039-020-01768-3

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  • DOI: https://doi.org/10.1007/s12039-020-01768-3

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