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

Young-Keun Yang; Jinsung Tae

doi:10.1055/s-2003-39319

LETTER

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;

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

For reviews on the synthesis of 1,2-oxazines by Diels-Alder reactions, see:

<A NAME="RU05203ST-1A">1a</A> Streith J. Defoin A. Synlett 1996, 198

<A NAME="RU05203ST-1B">1b</A> Denmark SE. Thorarensen A. Chem. Rev. 1996, 96: 137

<A NAME="RU05203ST-1C">1c</A> Vogt PF. Miller MJ. Tetrahedron 1998, 54: 1317

<A NAME="RU05203ST-2A">2a</A> Peglow T. Blechert S. Streckhan E. Chem. Commun. 1999, 433

<A NAME="RU05203ST-2B">2b</A> Schade W. Reissig H.-U. Synlett 1999, 632

<A NAME="RU05203ST-2C">2c</A> Shin I. Lee M.-R. Lee J. Jung M. Lee W. Yoon J. J. Org. Chem. 2000, 65: 7667

<A NAME="RU05203ST-2D">2d</A> Koenig SG. Leonard KA. Lowe RS. Austin DJ. Tetrahedron Lett. 2000, 41: 9393

<A NAME="RU05203ST-2E">2e</A> 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:

<A NAME="RU05203ST-3A">3a</A> Chang S. Grubbs RH. Tetrahedron 1998, 54: 4413

<A NAME="RU05203ST-3B">3b</A> Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012

<A NAME="RU05203ST-4A">4a</A> Koide K. Finkelstein ZB. Verdine GL. J. Am. Chem. Soc. 2001, 123: 398

<A NAME="RU05203ST-4B">4b</A> Miyabe H. Yoshida K. Matsumura A. Yamauchi M. Takemoto Y. Synlett 2003, 567

<A NAME="RU05203ST-5A">5a</A> Hu J. Miller MJ. Tetrahedron Lett. 1995, 36: 6379

<A NAME="RU05203ST-5B">5b</A> Oyama H, Morita T, and Ono T. inventors; Jap. Pat. Appl., JP 02229175. ; Chem. Abstr. 1991, 114, 81858

<A NAME="RU05203ST-5C">5c</A> Carruthers W. Johnstone RAW. J. Chem. Soc. 1965, 1653

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.

<A NAME="RU05203ST-7A">7a</A> Wolfe S, and Shustov GPCT. inventors; Int. Appl., WO 0311298. ; Chem. Abstr. 2003, 138, 153829

<A NAME="RU05203ST-7B">7b</A> Zong K. Shin SI. Kim HK. Kim HR. Jeon DJ. Ryu EK. Bull. Kor. Chem. Soc. 1999, 20: 965

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).

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

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