Subscribe to RSS
DOI: 10.1055/s-2003-39319
Synthesis of Heterocycles Containing an N-O Bond by Ring-Closing Metathesis of Dienes Tethered by Hydroxylamine
Publication History
Publication Date:
20 May 2003 (online)
Abstract
The dienes tethered by hydroxylamine were efficiently cyclized into 6- to 10-membered heterocycles containing an N-O bond by catalytic ring-closing metathesis.
Key words
cyclizations - heterocycles - metathesis - ring closure - ruthenium
- For reviews on the synthesis of 1,2-oxazines by Diels-Alder reactions, see:
-
1a
Streith J.Defoin A. Synlett 1996, 198 -
1b
Denmark SE.Thorarensen A. Chem. Rev. 1996, 96: 137 -
1c
Vogt PF.Miller MJ. Tetrahedron 1998, 54: 1317 -
2a
Peglow T.Blechert S.Streckhan E. Chem. Commun. 1999, 433 -
2b
Schade W.Reissig H.-U. Synlett 1999, 632 -
2c
Shin I.Lee M.-R.Lee J.Jung M.Lee W.Yoon J. J. Org. Chem. 2000, 65: 7667 -
2d
Koenig SG.Leonard KA.Lowe RS.Austin DJ. Tetrahedron Lett. 2000, 41: 9393 -
2e
Ishikawa T.Senzaki M.Kadoya R.Morimoto T.Miyake N.Izawa M.Saito S. J. Am. Chem. Soc. 2001, 123: 4607 - For reviews on metathesis, see:
-
3a
Chang S.Grubbs RH. Tetrahedron 1998, 54: 4413 -
3b
Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 -
4a
Koide K.Finkelstein ZB.Verdine GL. J. Am. Chem. Soc. 2001, 123: 398 -
4b
Miyabe H.Yoshida K.Matsumura A.Yamauchi M.Takemoto Y. Synlett 2003, 567 -
5a
Hu J.Miller MJ. Tetrahedron Lett. 1995, 36: 6379 -
5b
Oyama H,Morita T, andOno T. inventors; Jap. Pat. Appl., JP 02229175. ; Chem. Abstr. 1991, 114, 81858 -
5c
Carruthers W.Johnstone RAW. J. Chem. Soc. 1965, 1653 -
7a
Wolfe S, andShustov GPCT. inventors; Int. Appl., WO 0311298. ; Chem. Abstr. 2003, 138, 153829 -
7b
Zong K.Shin SI.Kim HK.Kim HR.Jeon DJ.Ryu EK. Bull. Kor. Chem. Soc. 1999, 20: 965
References
The Scifinder searches for 1,2-oxazonine, 1,2-oxazecine, and 3-oxo-6,7-dihydro-3H-[1,2]oxazepine hit no known related compounds.
8Spectral data for 8h: colorless oil; R f = 0.5 (hexane/EtOAc = 2:1); 1H NMR (250 MHz, CDCl3): δ = 5.64-5.53 (m, 2 H), 4.10-4.02 (t, J = 5.6 Hz, 2 H), 3.44-3.35 (t, J = 6.0 Hz, 2 H), 2.48-2.32 (m, 2 H), 2.36-2.24 (m, 2 H), 1.79-1.68 (m, 2 H), 1.49 (s, 9 H); 13C NMR (62.9 MHz, CDCl3): δ = 158.3, 130.8, 128.3, 81.2, 72.6, 52.7, 28.6, 26.2, 25.9, 23.0; IR (film, cm-1) 2971, 2931, 1729, 1709, 1459, 1393, 1368, 1337, 1164, 1123, 1082; MS: m/z (rel. intensity): 18 (7), 29 (10), 41 (20), 57 (100), 69 (7), 83 (8), 96 (15), 110 (3), 127 (10), 207 (M + , 1).