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Synthesis 2018; 50(18): 3738-3748
DOI: 10.1055/s-0037-1610415
DOI: 10.1055/s-0037-1610415
paper
The Acid-Catalyzed 2-O-Alkylation of Substituted 2-Hydroxy-1,4-naphthoquinones by Alcohols: Versatile Preparative Synthesis of Spinochrome D and Its 6-Alkoxy Derivatives
Further Information
Publication History
Received: 17 April 2018
Accepted after revision: 17 May 2018
Publication Date:
12 July 2018 (online)
Abstract
A series of substituted 2-alkoxy-1,4-naphthoquinone derivatives were obtained by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with propan-1-ol, butan-1-ol, or pentan-1-ol in good yields. Based on this reaction a versatile preparative synthesis of spinochrome D was developed.
Key words
2-hydroxy-1,4-naphthoquinones - acid catalysis - 2-O-alkylation - n-alkanol - spinochrome DSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610415.
- Supporting Information
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References
- 1a Thomson RH. Naturally Occurring Quinones . Academic Press; London: 1971. 2nd ed.
- 1b Thomson RH. Naturally Occurring Quinones . Chapman & Hall; London: 1987. 3rd ed
- 1c Thomson RH. Naturally Occurring Quinones IV . Blackie; London: 1997
- 2a Asche C. Mini-Rev. Med. Chem. 2005; 5: 449
- 2b Constantino L. Barlocco D. Curr. Med. Chem. 2006; 13: 65
- 2c Wellington KW. RSC Adv. 2015; 5: 20309
- 3a Service M. Wardlaw AC. Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. 1984; 79: 161
- 3b Sanchez-Calvo JM. Barbero GR. Guerrera-Vasquez G. Duran AG. Macıas M. Rodrıguez-Iglesias MA. Molinillo JM. G. Macıas FA. Med. Chem. Res. 2016; 25: 1274
- 4 Bringmann G. Rudenauer S. Irmer A. Bruhn T. Brun R. Heimberger T. Stuhmer N. Bargou R. Chatterjee M. Phytochemistry 2008; 69: 2501
- 5 El Hage S. Ane M. Stigliani J.-L. Marjorie M. Vial H. Baziard-Mouysset G. Payard M. Eur. J. Med. Chem. 2009; 44: 4778
- 6a Boguslavskaya LV. Khrapova NG. Maximov OB. Russ. Chem. Bull. 1985; 34: 1345
- 6b Lebedev AV. Ivanova MV. Levitsky DO. Life Sci. 2005; 76: 863
- 6c Lebedev AV. Ivanova MV. Levitsky DO. Hemoglobin 2008; 32: 165
- 7a Mishchenko NP. Fedoreev SA. Bagirova VL. Pharm. Chem. J. 2003; 37: 48
- 7b Tedeeva NS. Melnikov VY. Dogadova LP. Pacific Med. J. 2014; 7 ; http://tmj-vgmu.ru/index.php/en/ (in Russian)
- 7c Lennikov A. Kitaichi N. Noda K. Mizuuchi K. Ando R. Dong Z. Fukuhara J. Kinoshita S. Namba K. Ohno S. Ishida S. Mol. Vision 2014; 20: 171
- 8 Jeong SH. Kim HK. Song IS. Noh SJ. Marquez J. Ko KS. Rhee BD. Kim N. Mishchenko NP. Fedoreyev SA. Stonik VA. Han J. Mar. Drugs 2014; 12: 4602
- 9 Seo DY. McGregor RA. Noh SJ. Choi SJ. Mishchenko NP. Fedoreyev SA. Stonik VA. Han J. Mar. Drugs 2015; 13: 5722
- 10 Solitman AM. Mohamed AS. Marie AS. Austin J. Endocrinol. Diabetes 2016; 3: id1045 ; http://austinpublishinggroup.com/endocrinology-diabetes/
- 11 Schafer FQ. Qian SY. Buettner GR. Cell Mol. Biol. (Noisy-le-grand) 2000; 46: 657
- 12a Polonik SG. Tolkach AM. Uvarova NI. Zh. Org. Khim. 1994; 30: 248 ; Chem. Abstr. 1995, 122, 187894x
- 12b Anufriev VPh. Novikov VL. Maximov OB. Elyakov GB. Levitsky DO. Lebedev AV. Sadretdinov SM. Shvilkin AV. Afonskaya NI. Ruda MYa. Cherpachenko NM. Bioorg. Med. Chem. Lett. 1998; 8: 587
- 12c Polonik SG. Tolkach AM. Uvarova NI. Russ. J. Org. Chem. 1998; 34: 1172
- 12d Polonik SG. Russ. J. Org. Chem. 2009; 45: 1474
- 12e Eremenko EM. Antimonova OI. Shekalova OG. Polonik SG. Margulis BA. Guzhova IV. Cell Tiss. Biol. 2010; 4: 251
- 12f Yurchenko EA. Menchinskaya ES. Polonik SG. Agafonova IG. Guzhova IV. Margulis BA. Aminin DL. Med. Chem. (Henderson, NV, U. S.) 2015; 5: 263 ; https://www.omicsonline.org/medicinal-chemistry.php
- 13a Lien J.-C. Huang L.-J. Teng C.-M. Wang J.-P. Kuo S.-C. Chem. Pharm. Bull. 2002; 50: 672
- 13b Wang S.-H. Lo C.-Y. Gwo Z.-H. Lin H.-J. Chen L.-G. Kuo C.-D. Wu J.-Y. Molecules 2015; 20: 11994
- 13c Lu X. Altharawi A. Hansen EN. Long TE. Synthesis 2012; 44: 3225
- 14a Fieser LF. J. Am. Chem. Soc. 1926; 48: 2922
- 14b Bonifazi EL. Rhos-Luci C. Leyn LG. Burton G. Padryn JM. Misico RI. Bioorg. Med. Chem. 2010; 18: 2621
- 15a Moore RE. Singh H. Chang CW. J. Scheuer PJ. Tetrahedron 1967; 23: 3271
- 15b Anufriev VPh. Novikov VL. Malinovskaya GV. Glazunov VP. Synth. Commun. 1997; 27: 119
- 15c Sabutski YuE. Semenova MN. Yurchenko EA. Polonik NS. Denisenko VA. Dmitrenok PS. Semenov VV. Polonik SG. Nat. Prod. Commun. 2017; 12: 1081
- 16 March J. Advanced Organic Chemistry. Reactions, Mechanisms, and Structure . John Wiley & Sons; New York: 1985. 3rd ed. 789
- 17 Anderson HA. Smith J. Thomson RH. J. Chem. Soc. 1965; 2141
- 18 Balaneva NN. Shestak OP. Anufriev VP. Novikov VL. Chem. Nat. Compd. 2016; 52: 213
- 19 Pokhilo ND. Kiseleva MI. Machan’kov VV. Anufriev VPh. Chem. Nat. Compd. 2008; 44: 287
- 20a Polonik SG. Polonik NS. Denisenko VA. Moiseenko OP. Anufriev VF. Russ. J. Org. Chem. 2009; 45: 1410
- 20b Polonik NS. Anufriev VPh. Polonik SG. Nat. Prod. Commun. 2011; 6: 217
- 20c Polonik NS. Polonik SG. Denisenko VA. Moiseenko OP. Synthesis 2011; 3350
- 20d Polonik NS. Polonik SG. Tetrahedron Lett. 2017; 57: 3303
- 21a Fieser LF. Dunn JT. J. Am. Chem. Soc. 1937; 59: 1017
- 21b Singh H. Folk TL. Scheuer P. Tetrahedron 1969; 25: 5301
- 22a Anufriev VPh. Chizhova AYa. Denisenko VA. Novikov VL. Zh. Org. Khim. 1993; 29: 2008 ; Chem. Abstr. 1994, 120, 255376m
- 22b Pelageev DN. Panchenko MN. Pokhilo ND. Denisenko VA. Anufriev VF. Chem. Nat. Compd. 2008; 44: 719
- 23a Fieser LF. Oxford AE. J. Am. Chem. Soc. 1942; 64: 2060
- 23b Karnojitzki V. Les Peroxides Organiques . Hermann; Paris: 1958
- 23c Sabutskii YuE. Polonik SG. Denisenko VA. Dmitrenok PS. Synthesis 2014; 46: 2763
- 24 Pokhilo ND. Denisenko VA. Anufriev VF. Rus. J. Org. Chem. 2014; 50: 647