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
Download PDF
Synthesis 2003(5): 0662-0664
DOI: 10.1055/s-2003-38072
DOI: 10.1055/s-2003-38072
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York[4 + 1] Cycloaddition Reactions of o-Thioquinones with Isocyanides: Novel Syntheses of 2-Imino-1,3-Oxathioles
Further Information
Received
18 October 2002
Publication Date:
21 March 2003 (online)
Publication History
Publication Date:
21 March 2003 (online)
Abstract
o-Thioquinones, generated in situ from o-hydroxyphenylthiophthalimides, underwent facile [4 + 1] cycloaddition reactions with isocyanides to afford 2-imino-1,3-oxathioles.
Key words
thioquinones - isocyanides - cycloadditions - 2-imino-1,3-oxathioles
- 1a
Shabani A.Ajabi S.Farrokhzad F.Bijanzadch HR. J. Chem. Res., Synop. 1999, 582 ; and references cited therein - 1b
Kollenz G.Ott W.Ziegler E.Peters K.Schnering HGv.Quast H. Liebigs Ann. Chem. 1980, 1801 - 1c
Ott W.Kollenz G.Peters K.Peters E.-M.Schnering HGv.Quast H. Liebigs Ann. Chem. 1983, 635 - 1d
Figueroa-Villar JD.Carneiro CL.Cruz ER. Heterocycles 1992, 34: 891 - 1e
Rigby JH.Qabar M.Ahmed G.Hughess RC. Tetrahedron 1993, 49: 10219 - 1f
Buron C.Kaim LE.Uslu A. Tetrahedron Lett. 1997, 38: 8027 - 1g
Marcaccini S.Torroba T. Org. Prep. Proced. Int. 1993, 25: 143 - 1h
Morel G.Marchand E.Sinbandhit S.Carlier R. Eur. J. Org. Chem. 2001, 655 ; and the references cited therein - 2a
Nair V.Mathew B.Radhakrishnan KV.Rath NP. Synlett 2000, 61 - 2b
Nair V.Mathew B. Tetrahedron Lett. 2000, 41: 6919 - 2c
Nair V.Mathew B.Rath NP.Vairamani M.Prabhakar S. Tetrahedron 2001, 57: 8349 - 3 For earlier reports on cycloaddition
reaction of o-thioquinones see:
Capozzi G.Falciani C.Menichetti S.Nativi C. J. Org. Chem. 1997, 62: 2611 ; and the references cited therein - 4
Capozzi G.Menichetti S.Nativi C.Simonti MC. Tetrahedron Lett. 1994, 35: 9451 - 6a
Dunbar JE. inventors; US Patent 4349685. ; Chem. Abstr. 1982, 97, 216154 - 6b
Showa Denko KK. inventors; Jpn. Patent 6006680. ; Chem. Abstr. 1985, 102: 166730 - 6c
Aizawa Y.Kanai T.Hasegawa K.Yamaguchi T.Iizuka Y.Iwaoka T.Yoshioka T. J. Med. Chem. 1990, 33: 1491 - 7a
Ugi I.Meyr R.Lipinski M. In Organic Syntheses Vol 41:Roberts JD. John Wiley & Sons; New York: 1961. p.13 - 7b
Bredereck H.Fohlisch B.Walz K. Liebigs Ann. Chem. 1965, 686: 92
References
The ratio of the isomers was determined by the relative heights of the 13C signal of the carbon attached to the imino nitrogen.