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-00000083.xml
Synlett 2002(2): 0322-0324
DOI: 10.1055/s-2002-19763
DOI: 10.1055/s-2002-19763
LETTER
© Georg Thieme Verlag Stuttgart · New York
A New and Efficient Synthesis of Substituted 2-Hydroxymethyl-2-methyl-2H-chromenes
Further Information
Received
23 October 2001
Publication Date:
02 February 2007 (online)
Publication History
Publication Date:
02 February 2007 (online)
![](https://www.thieme-connect.de/media/synlett/200202/lookinside/thumbnails/10.1055-s-2002-19763-1.jpg)
Abstract
A new and efficient three step procedure for the synthesis of functionalized 2H-chromenes 1 is described, starting from commercially available salicylaldehydes 2 and 2-methylpropenylmagnesium chloride 3, which involves catalytic acid-mediated intramolecular cyclization of phenolic epoxide 5 as the key step.
Key words
2H-chromenes - chromenemethanols - 2,2-disubstituted 2H-chromenes - 2-hydroxymethyl-2-methyl-2H-chromenes - 2H-1-benzopyran
-
1a
Aizawa Y.Kanaï T.Fujita T.Yoshioka H.Yoshioka T. Heterocycles 1991, 32: 285 -
1b
Holley JH.Hadley KW.Turner CE. J. Pharm. Sci. 1975, 892 -
1c
Mc Hale D.Green J. J. Chem. & Ind. 1962, 1867 -
1d
Benslimane AF.Pouchus YF.Verbist JF.Petit JY.Brion JD.Welin L. J. Clin. Pharmacol. 1995, 35: 298 -
1e
Schweizer EE.Meeder-Nyez D. Chromenes, Chromanones and Chromones, 2H and 4H-1-BenzopyransEllis GP. John Wiley and sons; New York: 1977. Chap. II. p.81 ; and references cited therein -
1f
Dave E.Kusuni T.Ishitsuka M.Iwaschita T.Kakisawa H. Heterocycles 1984, 22: 2301 -
1g
Nomura T.Fukai T.Hano Y.Tsukamoto K. Heterocycles 1983, 20: 661 -
1h
Ellis GP. In The Chemistry of Heterocyclic Compounds, Chromenes, Chromanes, and ChromonesWeissberger A.Taylor EC. John Wiley; New York: 1977. Chap. II. p.13 - 2
Bouzbouz S.Goujon JY.Deplanne J.Kirschleger B. Eur. J. Org. Chem. 2000, 3223 - 3
Bell D.Davies MR.Green GR.Mann IS. Synthesis 1995, 707 -
4a
Rochfort SJ.Metzger R.Hobbs L.Capon RJ. Aust. J. Chem. 1996, 49: 1217 -
4b
Van Rensburg H.Van Heerden PS.Bezuidenhoudt BCB.Ferreira D. Tetrahedron Lett. 1997, 38: 3089 -
4c
Covington AD. Chem. Soc. Rev. 1997, 111 -
5a
Sukbok C.Grubbs RH. J. Org. Chem. 1998, 63: 864 -
5b
Chauder BA.Kalinin AV.Snieckus V. Synthesis 2001, 140 -
5c
Larock RC.Wei L.Hightowei TR. Synlett 1998, 522 -
5d
Solladié G.Boeffel D.Maignan J. Tetrahedron 1996, 52: 2065 -
5e
Chauder BA.Lopes CC.Lopes RSC.Da Silva AJM.Snieckus V. Synthesis 1998, 279 -
5f
Cruz-Almanza R.Perez-Florès F.Lemini C. Heterocycles 1994, 37: 759 -
5g
Garcias X.Ballester P.Saà JM. Tetrahedron Lett. 1991, 32: 7739 - 6
David M.Boustie J.Peilloux A.Poupon E.Amoros M.Sauleau A. Pharmaceutical Sciences 1997, 3: 305 - 7
Kocienski PJ. Protecting Groups Georg Thieme Verlag; New York NY: 1994.