A New and Convenient Synthesis of 1-Aryl-2-dimethylaminoethanols

Miklós Nyerges; Imre Fejes; Andrea Virányi; Paul W. Groundwater; László Töke

doi:10.1055/s-2001-16077

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

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

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2001(10): 1479-1482
DOI: 10.1055/s-2001-16077

PAPER

A New and Convenient Synthesis of 1-Aryl-2-dimethylaminoethanols

Miklós Nyerges*^a, Imre Fejes^a, Andrea Virányi^a, Paul W. Groundwater^b, László Töke^a
^a Research Group of the Hungarian Academy of Sciences, Department of Organic Chemical Technology, Technical University of Budapest, 1521 Budapest P.O.B. 91, Hungary
Fax: +36(1)4633648; e-Mail: nyerges.oct@chem.bme.hu;
^b Institute of Pharmacy and Chemistry, School of Sciences, University of Sunderland, Sunderland SR1 3SD, UK

Weitere Informationen

Publikationsverlauf

Received 8 February 2001
Publikationsdatum:
23. September 2004 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

An efficient two-step synthesis of 1-aryl-2-dimethylaminoethanols 4 is described, consisting of oxazolidine 3 generation from the cycloaddition of an azomethine ylide to an aldehyde, followed by reductive ring-opening.

Key words

aldehydes - amino alcohols - cycloadditions

References

1 Lednicer D. Mitcher LA. The Organic Chemistry of Drug Synthesis Vol. 2: Wiley; New York: 1980.

Google Scholar
2 For a recent review, see: Bergmeier SC. Tetrahedron 2000, 56: 2561

Crossref Google Scholar
See for example:
3a Philippo C. Fett E. Bovy P. Barras M. Angel I. Eur. J. Med. Chem. Chim. Ther. 1997, 881

Crossref Google Scholar
3b Park BK. Haynes BP. Sheridan SA. Nowell PT. J. Pharm. Pharmacol. 1983, 35: 373

Crossref Google Scholar
3c Yamada K. Shirahata S. Murakami H. Nishiyama K. Shinohara K. Omura H. Agric. Biol. Chem. 1985, 49: 1423

Crossref Google Scholar
3d Alpatova TV. Klimova AD. Kulinskii VI. Mirzoyan VS. Mirzoyan AT. Yashunskii VG. Pharm. Chem. J. (Engl. Transl.) 1984, 18: 262

Crossref Google Scholar
Crossref Google Scholar
4a Chapman NB. Triggle DJ. J. Chem. Soc. 1963, 1385

Google Scholar
4b Soai K. Niwa S. Kobayashi T. J. Chem. Soc., Chem. Commun. 1987, 801

Google Scholar
4c Miyano S. Lu LD.-L. Viti SM. Sharpless KB. J. Org. Chem. 1985, 50: 4350

Google Scholar
4d Raposo C. Wilcox CS. Tetrahedron Lett. 1999, 40: 1285

Google Scholar
4e Patel PJ. Messer WS. Hudson RA. J. Med. Chem. 1993, 36: 1893

Google Scholar
4f Chapman NB. Allen J. J. Chem. Soc. 1960, 1482

Google Scholar
5a Leonard NJ. Klainer JA. J. Heterocycl. Chem. 1971, 8: 215

Google Scholar
5b Hopff K. Keller H. Helv. Chim. Acta 1959, 42: 2457

Google Scholar
5c Brown HC. Pai GG. J. Org. Chem. 1983, 48: 1784

Google Scholar
6a Ishibashi H. Miki Y. Ikeda Y. Kiriyama A. Ikeda M. Chem. Pharm. Bull. 1989, 37: 3396

Google Scholar
6b Wright JB. Gutsell ES. J. Org. Chem. 1959, 24: 265

Google Scholar
7 Rudas M. Fejes I. Nyerges M. Szöllõssy A. Töke L. Groundwater PW. J. Chem. Soc., Perkin Trans. 1 1999, 1167

Crossref Google Scholar
8a Tsuge O. Kanemasa S. Ohe M. Takenaka S. Bull. Chem. Soc. Jpn. 1987, 60: 4079

Crossref Google Scholar
8b Ardill H. Grigg R. Sridharan V. Surendrakumar S. Thianpatanagul S. Kanajun S. J. Chem. Soc., Chem. Commun. 1986, 602

Crossref Google Scholar
8c Orsini F. Pellizzoni F. Forte M. Destro R. Gariboldi P. Tetrahedron 1988, 44: 519

Crossref Google Scholar
8d Rizzi GR. J. Org. Chem. 1970, 35: 2069

Crossref Google Scholar
9 Tsuge O. Hatta T. Tashiro H. Kakura Y. Maeda H. Kakehi H. Tetrahedron 2000, 56: 7723

Crossref Google Scholar