Abstract
An efficient and modern method for the preparation of amidoalkyl naphthols in the presence of silica nanoparticle-supported ferric chloride under thermal solvent-free conditions is explained. The prepared amidoalkyl naphthols were converted to 1,3-oxazines by Vilsmeier reagent in the presence of FeCl3/SiO2 nanoparticles. This method provides a novel route to synthesis amidoalkyl naphthol and 1,3-oxazine derivatives in terms of good yields, short reaction times, and recyclable catalyst.
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Sasaki K, Kusakabe Y, Esumi S (1972) J Antibiot 25:151
Johnson PY, Silver RB (1975) J Heterocycl Chem 10:1029
Lesher GY, Surrey AR (1955) J Am Chem Soc 77:636
Mosher HS, Frankel MB, Gregory M (1953) J Am Chem Soc 75:5326
Ren H, Grady S, Gamenara D, Heinzen H, Moyna P, Croft S, Kendrick H, Yardley V, Moyna G (2001) Bioorg Med Chem Lett 11:1851
Benedini F, Bertolini G, Cereda R, Doná G, Gromo G, Levi S, Mizrahi J, Sala A (1995) J Med Chem 38:130
Clark RD, Caroon JM, Kluge AF, Repke DB, Roszkowski AP, Strosberg AM, Baker S, Bitter SM, Okada MD (1983) J Med Chem 26:657
Matsuoka H, Ohi N, Mihara M, Suzuki H, Miyamoto K, Maruyama N, Tsuji K, Kato N, Akimoto T, Takeda Y, Yano K, Kuroki T (1997) J Med Chem 40:105
Khumtaveeporn K, Alper H (1995) J Org Chem 60:8142
Damodiran M, Panneer Selvam N, Perumal PT (2009) Tetrahedron Lett 50:5474
Tabuchi Y, Ando Y, Kanemura H, Kawasaki I, Ohishi T, Koida M, Fukuyama R, Nakamuta H, Ohta S, Nishide K, Ohishi Y (2009) Bioorg Med Chem 17:3959
Khodaei MM, Khosropour AR, Moghanian H (2006) Synlett 916
Patil SB, Singh PR, Surpur MP, Samant SD (2007) Ultrason Sonochem 14:515
Ansari SAMK, Sangshetti JN, Kokare ND, Wakte PS, Shinde DB (2010) Indian J Chem Technol 17:71
Shaterian HR, Yarahmadi H, Ghashang M (2008) Bioorg Med Chem Lett 18:788
Su WK, Tang WY, Li JJ (2008) J Chem Res 123
Das B, Laxminarayana K, Ravikanth B, Rao BR (2007) J Mol Catal A: Chem 261:180
Nagarapu L, Baseeruddin M, Apuri S, Kantevari S (2007) Catal Commun 8:1729
Jiang WQ, An LT, Zou JP (2008) Chin J Chem 26:1697
Kumar A, Rao MS, Ahmad I, Khungar B (2009) Can J Chem 87:714
Patil SB, Singh PR, Surpur MP, Samant SD (2007) Synth Commun 37:1659
Kantevari S, Vuppalapati SVN, Nagarapu L (2007) Catal Commun 8:1857
Sabitha G, Arundhathi K, Sudhakar K, Sastry BS, Yadav JS (2010) J Heterocycl Chem 47:272
Shaterian HR, Khorami F, Amirzadeh A, Ghashang M (2009) Chin J Chem 27:815
Chavan NL, Naik PN, Nayak SK, Kusurkar RS (2010) Synth Commun 40:2941
Zhang P, Zhang ZH (2009) Monatsh Chem 140:199
Khabazzadeh H, Saidi K, Seyedi N (2009) J Chem Sci 121:429
Shaterian HR, Yarahmadi H (2008) Tetrahedron Lett 49:1297
Supale AR, Gokavi GS (2010) J Chem Sci 122:189
Wang M, Liang Y (2011) Monatsh Chem 142:153
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The authors are grateful to Islamic Azad University, Qom Branch, for financial support of this work.
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Ghomi, J.S., Zahedi, S. Eco-friendly synthesis of highly substituted functionalized oxazines by FeCl3/SiO2 nanoparticles. Monatsh Chem 144, 687–693 (2013). https://doi.org/10.1007/s00706-012-0850-1
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DOI: https://doi.org/10.1007/s00706-012-0850-1