Synlett 2003(7): 1043-1045
DOI: 10.1055/s-2003-39319
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Heterocycles Containing an N-O Bond by Ring-Closing Meta­thesis of Dienes Tethered by Hydroxylamine

Young-Keun Yang, Jinsung Tae*
Department of Chemistry, Yonsei University, Seoul 120-749, Korea
Fax: +82(2)3647050; e-Mail: jstae@yonsei.ac.kr;
Further Information

Publication History

Received 15 March 2003
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.

6

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.

8

Spectral 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).