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 2010(4): 628-632
DOI: 10.1055/s-0029-1219365
DOI: 10.1055/s-0029-1219365
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
New Regiospecific Catalytic Approaches to 4,5-Dihydroisoxazoles and 2,5-Dihydroisoxazoles from O-Propargylic Hydroxylamines
Further Information
Received
9 November 2009
Publication Date:
02 February 2010 (online)
Publication History
Publication Date:
02 February 2010 (online)
![](https://www.thieme-connect.de/media/synlett/201004/lookinside/thumbnails/10.1055-s-0029-1219365-1.jpg)
Abstract
Unprotected O-propargylic hydroxylamines undergo generally essentially quantitative cyclisations when exposed briefly to silver nitrate adsorbed onto silica gel to give 4,5-dihydroisoxazoles [2-isoxazolines], while N-protected derivatives give the corresponding 2,5-dihydroisoxazoles [3-isoxazolines] in similarly excellent yields, given that an appropriate functionality on nitrogen is used.
Key words
4,5- and 2,5-dihydroisoxazoles - O-propargylic hydroxylamines - cyclisations - silver nitrate on silica gel
- For reviews of previous syntheses of dihydroisoxazoles, see:
-
1a
Lang SA.Lin Y.-I. Comp. Heterocycl. Chem. Vol. 6:Katritzky AR.Rees CW. Pergamon Press; Oxford: 1984. p.1 -
1b
Sutharchanadevi M.Muragan R. Comp. Heterocycl. Chem. II Vol. 6:Katritzky AR.Rees CW.Scriven EFV. Elsevier Science Ltd.; Oxford: 1996. p.253 -
1c
Cicchi S.Cordero FM.Giomi D. Prog. Heterocycl. Chem. 2003, 15: 261 - See, for example:
-
2a
Groutas WC.Venkataramam R.Chong LS.Yoder JE.Epp JB.Stanga MA.Kim E.-H. Bioorg. Med. Chem. 1995, 3: 125 -
2b
Pruitt JR.Pinto DJ.Estrella MJ.Bostrom LL.Knabb RM.Wong PC.Wright MR.Wexler RR. Bioorg. Med. Chem. 2000, 10: 685 -
2c
Conti P.Amici MD.Roda G.Vistoli G.Stensbol TB.Bräuner-Osborne H.Madsen U.Toma L.Micheli CD. Tetrahedron 2003, 59: 1443 -
3a
Cremonesi G.Croce PD.Fontana F.Fiorelli C.La Rosa C. Tetrahedron: Asymmetry 2008, 19: 2850 -
3b
Kozikowski AP.Adamczyk M. Tetrahedron Lett. 1982, 23: 3123 -
3c
Curran DP. J. Am. Chem. Soc. 1983, 105: 5826 -
3d
Curran DP.Scanga S.Fenk C. J. Org. Chem. 1984, 49: 3474 -
3e
Jäger V.Schwab V.Buss W. Angew. Chem., Int. Ed. Engl. 1981, 20: 601 - For reviews, see:
-
4a
Pellissier H. Tetrahedron 2007, 63: 3235 -
4b
Gothelf KV.Jorgensen KA. Chem. Rev. 1998, 98: 863 ; and references therein -
4c For a very recent contribution,
see:
Almeida V.dos Santos RJ.da Silva AJ.de Lima JG.Correia CRD.de Faria AR. Tetrahedron Lett. 2009, 50: 684 - For some mechanistically related preparations of 4,5-dihydroisoxazoles, see:
-
5a
Cwik A.Hell Z.Fuchs A.Halmai D. Tetrahedron Lett. 2005, 46: 6563 -
5b
Cecchi L.De Sarlo F.Machetti F. Synlett 2007, 2451 -
5c
Cecchi L.De Sarlo F.Machetti F. Chem. Eur. J. 2008, 14: 7093 - See, for example:
-
6a
Ros A.Alvarez E.Dietrich H.Fernández R.Lassaletta JM. Synlett 2005, 2899 -
6b
Brinkmann Y.Madhushaw RJ.Jazzer R.Bernardinelli G.Künig EP. Tetrahedron 2007, 63: 8413 -
6c
Suga H.Adachi Y.Fujimoto K.Furihata Y.Tsuchida T.Kakehi A.Baba T. J. Org. Chem. 2009, 74: 1099 - 7
Norman AL.Shurrush KA.Calleroz AT.Mosher MD. Tetrahedron Lett. 2007, 48: 6849 -
8a
Rodriguez-Franco MI.Dorronsoro I.Martinez A. Synthesis 2001, 1711 -
8b
Pennicott L.Lindell S. Synlett 2006, 463 -
8c See also:
Davies SG.Jones S.Sanz MA.Teixeira FC.Fox JF. Chem. Commun. 1998, 2235 - 9
Norman AL.Mosher MD. Tetrahedron Lett. 2008, 49: 4153 - 10
Mosher MD.Norman AL.Shurrush KA. Tetrahedron Lett. 2009, 50: 5647 -
11a
Debleds O.Dal Zotto C.Vrancken E.Campagne JM.Retailleau P. Adv. Synth. Catal. 2009, 351: 1991 -
11b See also:
Georgy M.Boucard V.Debleds O.Dal Zotto C.Campagne J.-M. Tetrahedron 2009, 65: 1758 - 12
Winter C.Krause N. Angew. Chem. Int. Ed. 2009, 48: 6339 - 13
Zielinska-Bajet M.Kowalczyk R.Skarzewski J. Tetrahedron 2005, 61: 5235 - 14
Stepakov AV.Galkin IA.Kostikov RR.Starova GL.Starikova ZA.Molchanov AP. Synlett 2007, 1235 - 15
Yeom H.-S.Lee E.-S.Shin S. Synlett 2007, 2292 - 16
Knight DW. Prog. Heterocycl. Chem. Vol. 14:Gribble GW.Gilchrist TL. Elsevier Scientific Ltd.; Oxford: 2002. p.19 - 17
Foot OF.Low ACL.Knight DW.Li Y.-F. Tetrahedron Lett. 2007, 48: 647 - 18
Huang X.Tang E. J. Chem. Res. 2004, 32 - 19
Aschwanden P.Frantz DE.Carreira EM. Org. Lett. 2000, 2: 2331 - 20
Aschwanden P.Kvaernø L.Geisser RW.Kleinbeck F.Carreira EM. Org. Lett. 2005, 7: 5741 - 21
Hayes SJ.Knight DW.Menzies MD.O’Halloran M.Tan W.-F. Tetrahedron Lett. 2007, 48: 7709 -
22a
Dalla V.Pale P. New. J. Chem. 1999, 23: 803 -
22b For a review of the use
of silver(I) salts in heterocyclic synthesis, see:
Weibel JM.Blanc A.Pale P. Chem. Rev. 2008, 108: 3149 - 23
Proctor AJ.Beautement K.Clough JM.Knight DW.Li Y. Tetrahedron Lett. 2006, 47: 5151 -
24a
Grochowski E.Jurczak J. Synthesis 1976, 682 -
24b
Iwagami H.Yatagai M.Nakazawa M.Orita H.Honda Y.Ohnuki T.Yukawa T. Bull. Chem. Soc. Jpn. 1991, 64: 175
References
Hatherley J. L., Knight D. W. unpublished observations.