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Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water

Year 2015, Volume: 43 Issue: 2, 127 - 132, 01.06.2015

Abstract

Asimple and facile synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4 1H -one derivatives has been successfully developed by treatment of aldehydes, ammonium acetate, and isatoic anhydride under reflux conditions in the presence of a squaric acid organocatalyst. These catalytic condensation reactions represent green chemical processes and the squaric acid organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction.

References

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  • S. Khaksar, M. Yaghoobi, J. Fluorine. Chem., 41, (2012), 142.
  • S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluorine. Chem., 11 (2012) 141.
  • S. Khaksar, M. Tajbakhsh, M. Gholami, F. Rostamnezhad, Chin.Chem.Lett., 1287 (2014) 25.

Yeni Sulu Organokatalizör Skuarik Asit Varlığında Mono ve Disübstitüye 2,3-Dihidroksikuinazolin- 4 1H -Ones’un Etkin ve

Year 2015, Volume: 43 Issue: 2, 127 - 132, 01.06.2015

Abstract

A ldehitler, amonyum asetat ve izotaktik anhidrit muameleleriyle skuarik asit organokatalizörü varlığında geri soğutucu altında, mono ve disübstitiye 2,3-dihidrokinazolin -4 1H türevlerinin sentezi başarılı bir şekilde gerçekleştirilmiştir. Bu katalitik yoğuşma tepkimeleri yeşil kimya süreçlerini kapsamaktadır. Skuarik asit organokatalizörü havada kararlı, uygun maliyetli ve kullanımı kolaydır. Ayrıca tepkime ortamından kolaylıkla uzaklaştırılabilir

References

  • Y.S. Sadanadam, R.M. Reddy, A. Bhaskar, Eur. J. Med. Chem., 169 (1987) 22.
  • G. Bonola, E. Sianesi, J. Med. Chem., 329 (1970) 13.
  • M.L. Hour, L. Huang, S. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K. Lee, J. Med. Chem., 4479 (2000) 43.
  • S. H. Lee, S. Y. Jung, H. A. Park, H. B. Kang, J. Kim, D. J. Choo, A. Handforth, J. Y. Lee, Bull. Korean. Chem. Soc., 2451 (2010) 31.
  • P. A. Ple, T. P.Green, L. F. Hennequin, J. Curwen, M. Fennell, J. Allen, Brempt, C. L. Costello, G. J. Med. Chem., 871 (2004) 47.
  • H. N. Seo, J. Y. Choi, Y. J. Choe, Y. Kim, H. Rhim, S. H. Lee, J. Kim, D. J. Joo and J. Y. Lee, Bioorg. Med. Chem. Lett., 5740 (2007) 17. 7. M. Baghbanzadeh, P. Salehi, M. Dabiri, G. Kozehgarya, Synthesis, (2006) 344. Kozehgarya, A. A. Mohammadi, Tetrahedron Lett., 6123 (2005) 46.
  • P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth.Commun., 2287 (2006) 36.
  • J. X. Chen, W. K. Su, H. Y. Wu, M. C. Liu, C. Jin. Green Chem., 972 (2007) 9.
  • J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su. Tetrahedron Lett., 3814 (2008) 49.
  • P. Salehi, M. Dabiri, M. A. Zolfigol, M. Baghbanzadeh, Synlett., (2005) 1155.
  • H. L. J. Yale, Heterocycl. Chem., 1357 (1977), 14.
  • M. R. Mousavi, M. T. Maghsoodlou, J. Iranian. Chem. Soc., 743 (2015) 12.
  • A. Chanda, V. V. Fokin, Chem. Rev., 725 (2009) 109.
  • S. Minakata, M. Komatsu, Chem. Rev., 711 (2009) 109.
  • G. V. Oshovsky, D. N. Reinhoudt, W. Verboom, Angew. Chem. Int. Ed., 2366 (2007) 46.
  • C.J. Li, Chem. Rev., 3095 (2005) 105.
  • V. M. Dong, D. Fiedler, B. Cari, R. G. Bergmann, K. N. Raymond, J. Am. Chem. Soc., 14464 (2006) 128.
  • P.I. Dalko, L. Moisan, Angew. Chem. Int. Ed., 3726 (2001),40.
  • P.I. Dalko, L. Moisan, Angew. Chem. Int. Ed., 5138 (2004),43. Ed., 1570 (2007) 46.
  • N. Azizi, A. Davoudpour, F. Eskandari, E. Batebi, Monatsh. Chem., 405 (2013) 144.
  • N. Azizi, E. Saki, M. Edrisi, C R Chimie., 973 (2011) 14.
  • N. Azizi, A. Davoudpour, Catalysis Lett., 1506 (2011) 141.
  • R. I. Storer, C. Aciroa, L. H. Jones, Chem. Soc. Rev., 40 (2011) 2330.
  • S. Khaksar, M. Yaghoobi, J. Fluorine. Chem., 41, (2012), 142.
  • S. Khaksar, A. Rouhollahpour, S.M. Talesh, J. Fluorine. Chem., 11 (2012) 141.
  • S. Khaksar, M. Tajbakhsh, M. Gholami, F. Rostamnezhad, Chin.Chem.Lett., 1287 (2014) 25.
There are 26 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Samad Khaksar This is me

Sattar Arshadi This is me

Fatemeh Ghanbari This is me

Publication Date June 1, 2015
Published in Issue Year 2015 Volume: 43 Issue: 2

Cite

APA Khaksar, S., Arshadi, S., & Ghanbari, F. (2015). Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water. Hacettepe Journal of Biology and Chemistry, 43(2), 127-132.
AMA Khaksar S, Arshadi S, Ghanbari F. Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water. HJBC. June 2015;43(2):127-132.
Chicago Khaksar, Samad, Sattar Arshadi, and Fatemeh Ghanbari. “Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid As a New Organocatalyst in Water”. Hacettepe Journal of Biology and Chemistry 43, no. 2 (June 2015): 127-32.
EndNote Khaksar S, Arshadi S, Ghanbari F (June 1, 2015) Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water. Hacettepe Journal of Biology and Chemistry 43 2 127–132.
IEEE S. Khaksar, S. Arshadi, and F. Ghanbari, “Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water”, HJBC, vol. 43, no. 2, pp. 127–132, 2015.
ISNAD Khaksar, Samad et al. “Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid As a New Organocatalyst in Water”. Hacettepe Journal of Biology and Chemistry 43/2 (June 2015), 127-132.
JAMA Khaksar S, Arshadi S, Ghanbari F. Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water. HJBC. 2015;43:127–132.
MLA Khaksar, Samad et al. “Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid As a New Organocatalyst in Water”. Hacettepe Journal of Biology and Chemistry, vol. 43, no. 2, 2015, pp. 127-32.
Vancouver Khaksar S, Arshadi S, Ghanbari F. Efficient and Green Synthesis of Mono- and Disubstituted 2,3-Dihydroquinazolin-4 1H -Ones Using Squaric Acid as a New Organocatalyst in Water. HJBC. 2015;43(2):127-32.

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