Abstract
An efficient synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-diones from the three-component condensation reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine, aromatic aldehydes, and 2-hydroxy-1,4-naphthoquinone under solvent-free conditions in good to excellent yields and short reaction times using sulfamic acid as heterogeneous acid catalyst has been investigated.
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El-Sayed OA, Aboul-Enein HY (2001) Arch Pharm 334:117
Wolin R, Wang D, Kelly J, Afonso A, James L, Kirschmeier P, McPhail AT (1996) Bioorg Med Chem Lett 6:195
He Z, Milburn GHW, Baldwin KJ, Smith DA, Danel A, Tomasik P (2000) J Lumin 86:1
Tomasik P, Tomasik D, Abramovitch RA (1983) J Heterocycl Chem 20:1539
Chaczatrian K, Chaczatrian G, Danel A, Tomasik P (2001) Arkivoc vi:63
Danel A, Chaczatrian K, Tomasik P (2000) Arkivoc i:51
Quiroga J, Insuasty B, Saitz C, Jullian C (1998) J Heterocycl Chem 35:575
Hua GP, Xu JN, Tu SJ, Wang Q, Zharlg JP, Zhu XT, Li TJ, Zhu SL, Zhang X (2005) J Chin Org Chem 25:1610
Jin TS, Sun G, Li YW, Li TS (2002) Green Chem 4:255
Nagarajan R, Magesh CJ, Perumal PT (2004) Synthesis 69
Rajitha B, Sunil Kumar B, Thirupathi Reddy Y, Narsimha Reddy P, Sreenivasulu N (2005) Tetrahedron Lett 46:8691
Venu Madhav J, Naveen Kumar Rajitha VB (2008) Synth Commun 38:1799
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We are pleased to acknowledge the financial support from Xinxiang Medical University.
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Wu, L., Ma, S., Yan, F. et al. Sulfamic-acid-catalyzed simple and efficient synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-diones under solvent-free conditions. Monatsh Chem 141, 565–568 (2010). https://doi.org/10.1007/s00706-010-0282-8
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DOI: https://doi.org/10.1007/s00706-010-0282-8