Selective Monomethylation of
Quercetin

Zhong-hua Zhou; Zhuan Fang; Hui Jin; Yue Chen; Ling He

doi:10.1055/s-0030-1258310

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(23): 3980-3986
DOI: 10.1055/s-0030-1258310

PAPER

Selective Monomethylation of Quercetin

Zhong-hua Zhou^a, Zhuan Fang^a, Hui Jin^a, Yue Chen^b, Ling He*^a
^a Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China
^b Department of Nuclear Medicine Affiliated Hospital, Luzhou Medical College, No. 25 Taiping Street, Luzhou, Sichuan, 646000, P. R. of China
Fax: +86(28)85503365.; e-Mail: lhe2001@sina.com;

Further Information

Publication History

Received 24 June 2010
Publication Date:
21 October 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Quercetin was monomethylated under mild conditions in moderate yields through selective deprotection. The combined effects of the protecting group and the heating mode on the reactivity were investigated. The presence of borax and the use of microwave irradiation significantly improved the yield and selectivity of alkylation.

Key words

alkylations - regioselectivity - methylation - heterocycles - quercetin

References

1 Manthey JA. Grohmann K. Montanari A. Ash K. Manthey CL. J. Nat. Prod. 1999, 62: 441

Crossref Google Scholar
2 Marrero PY. J. Chem. Inf. Comput. Sci. 2004, 44: 2010

Crossref Google Scholar
3 Peng W.-J. Li Y.-W. Zhu C.-S. Han X.-W. Yua B. Carbohydrate Res. 2005, 340: 1682

Crossref Google Scholar
4 Hosny M. Dhar K. Rosazza JPN. J. Nat. Prod. 2001, 64: 462

Crossref Google Scholar
5 Jurd L. J. Org. Chem. 1962, 27: 1294

Crossref Google Scholar
6 Needs PW. Kroon PA. Tetrahedron 2006, 62: 6862

Crossref Google Scholar
7 Li H.-J. Luan X.-H. Zhao Y.-M. Youji Huaxue 2004, 24: 1619

Google Scholar
8 Bouktaib M. Lebrun S. Atmani A. Rolando C. Tetrahedron 2002, 58: 10001

Crossref Google Scholar
9 He L. Yu J. Zhang J. Yu X.-Q. Org. Lett. 2007, 9: 2277

Crossref Google Scholar
10 He L. Wang Q. Zhou G.-C. Guo L. Yu X.-Q. ARKIVOC 2008, (xii): 103

Google Scholar
11 Jain AC. Pankajamani KS. Seshadri TR. J. Sci. Ind. Res. 1953, 127

Google Scholar
12 Emri J. Gyori B. In Comprehensive Coordination Chemistry Vol. 3: Wilkinson G. Gillard RD. McCleverty JA. Pergamon; Oxford: 1987. Chap. 24. p.81 ; and references cited therein

Google Scholar
13 Lorand JP. Edwards JO. J. Org. Chem. 1959, 24: 769

Crossref Google Scholar
14 Yoshino K. Kotaka M. Okamoto M. Kakihana H. Bull. Chem. Soc. Jpn. 1979, 52, 3005

Google Scholar
15 Hu G. Huang L. Huang R.-H. Wulff WD. J. Am. Chem. Soc. 2009, 131: 15615

Google Scholar
16 Caldwell ST. Crozier A. Hartley RC. Tetrahedron. 2000, 56: 4101

Crossref Google Scholar
17 Pacheco H. Grouiller A. Bull. Soc. Chim. Fr. 1965, 3: 779

Google Scholar
18 Jin C.-R. Ma D.-Z. Wang Y.-H. Feng H.-X. Huaxi Yaoxue Zazhi 1986, 1: 152

Google Scholar
19 Itokawa H. Suto K. Takeya K. Chem. Pharm. Bull. 1981, 29: 254

Google Scholar