Synthesis of N4-substituted[1,3,4]oxadiazinan-2-ones derived from norephedrine

被引：9

作者：

Casper, DM ^{[1
]}

Nora, GP ^{[1
]}

Blackburn, JR ^{[1
]}

Bentley, JT ^{[1
]}

Taylor, DC ^{[1
]}

Hitchcock, SR ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Normal, IL 61790 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2002年 / 39卷 / 04期

关键词：

D O I：

10.1002/jhet.5570390431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[1,3,4]-Oxadiazinan-2-ones bearing substitution at the N-4-position have been synthesized from norephedrine in good yield via N-alkylation, nitrosation, reduction and cyclization.

引用

页码：823 / 828

页数：6

共 12 条

[1] STUDIES ON ASYMMETRIC SYNTHESIS OF ALPHA-AMINO ACIDS .1. A NEW APPROACH [J].

COREY, EJ ;

MCCAULLY, RJ ;

SACHDEV, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2476-+

[2] 5-ALKOXY(ARALKOXY)-3,6-DIHYDRO-2H-1,3,4-OXADIAZIN-2-ONES(THIONES) FROM 2-HYDROXYCARBOHYDRAZONO ESTERS [J].

GEFFKEN, D ;

HOLST, C .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1994, 49 (07) :970-976

[3] X-ray crystallographic and 13C nuclear magnetic resonance studies of 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones derived from ephedrine and pseudoephedrine [J].

Hitchcock, SR ;

Nora, GP ;

Casper, DM ;

Squire, MD ;

Maroules, CD ;

Ferrence, GM ;

Szczepura, LF ;

Standard, JM .

TETRAHEDRON, 2001, 57 (49) :9789-9798

[4] X-ray crystallographic and proton nuclear magnetic resonance studies of β-hydroxy-N-nitrosamines derived from α-amino acids and ephedrine [J].

Hitchcock, SR ;

Nora, GP ;

Hedberg, C ;

Casper, DM ;

Buchanan, LS ;

Squire, MD ;

West, DX .

TETRAHEDRON, 2000, 56 (45) :8799-8807

[5] PREPARATION OF 2-ARYL-4A,5-DIHYDRO-4H-[1,3,4]OXADIAZINO[4,5-A]INDOLES AS A [A]-FUSED INDOLE-DERIVATIVES [J].

KANEKO, K ;

WATANABE, K ;

GOKITA, M ;

TORISAWA, K ;

TAKEDA, A ;

KATO, A ;

KATAYAMA, H .

HETEROCYCLES, 1994, 37 (03) :1645-1656

[6] SELECTIVE REDUCTION OF CARBOXYLIC-ACIDS INTO ALCOHOLS USING NABH4 AND I2 [J].

KANTH, JVB ;

PERIASAMY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5964-5965

[7]

KENNON MJ, 1993, J ORG CHEM, V58, P3568

[8]

Lawley PD, 1984, ACS MONOGRAPH, V182

[9]

Loeppky RN, 1994, ACS S SERIES, V553

[10]

Myers AG, 1999, ORG SYNTH, V76, P57

← 1 2 →