CONVENIENT SYNTHESIS OF 4-METHYLENE-2-OXAZOLIDINONES AND 4-METHYLENETETRAHYDRO-1,3-OXAZIN-2-ONES VIA TRANSITION-METAL-CATALYZED INTRAMOLECULAR ADDITION OF NITROGEN ATOM TO ACETYLENIC TRIPLE BOND

被引：52

作者：

TAMARU, Y ^{[1
]}

KIMURA, M ^{[1
]}

TANAKA, S ^{[1
]}

KURE, S ^{[1
]}

YOSHIDA, Z ^{[1
]}

机构：

[1] KYOTO UNIV, FAC ENGN, DEPT SYNTHET CHEM, SAKYO KU, KYOTO 606, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 10期

关键词：

D O I：

10.1246/bcsj.67.2838

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Propynyl tosylcarbamates 1 undergo cyclization smoothly by the catalysis of CuCl/Et3N or AgNCO/Et3N to furnish 4-methylene-2-oxazolidinones 2 in good yields. The similar cyclization of the N-acyl derivatives of 1 (PhCO, MeCO, EtOCO, etc.) is catalyzed effectively by AgNCO/t-BuOK. These reactions accommodate a variety of substituents at C1 and C3 of 2-propyn-1-ol and provide (Z)-2 as single stereoisomers. The scope of the cyclization of 3-butynyl carbamates is rather limited, and in general only N-tosyl derivatives of terminally unsubstituted 3-butyn-1-ols undergo cyclization to give 4-methylenetetrahydro-1,3-oxazin-2-ones in synthetically useful yields by the catalysis of AgNCO/Et3N or AgNCO/t-BuOK.

引用

页码：2838 / 2849

页数：12

共 53 条

[21] TOTAL SYNTHESIS AND X-RAY STRUCTURE DETERMINATION OF CYANOBACTERIN [J].

JONG, TT ;

WILLIARD, PG ;

PORWOLL, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (04) :735-736

[22]

JOUMIER JM, 1992, SYNLETT, P453

[23] FUNCTIONAL CARBONATES - CYCLIC ALPHA-METHYLENE CARBONATES AND BETA-OXOPROPYL CARBONATES FROM PROP-2-YNYL ALCOHOL DERIVATIVES AND CO2 [J].

JOUMIER, JM ;

FOURNIER, J ;

BRUNEAU, C ;

DIXNEUF, PH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3271-3274

[24] CONVENIENT SYNTHESIS OF DENSELY FUNCTIONALIZED N-SUBSTITUTED 4-METHYLENE-2-OXAZOLIDINONE [J].

KIMURA, M ;

KURE, S ;

YOSHIDA, Z ;

TANAKA, S ;

FUGAMI, K ;

TAMARU, Y .

TETRAHEDRON LETTERS, 1990, 31 (34) :4887-4890

[25]

LAAS H, 1980, Patent No. 2834607

[26] PALLADIUM(II) CATALYZED CYCLIZATION OF ALKYNOIC ACIDS [J].

LAMBERT, C ;

UTIMOTO, K ;

NOZAKI, H .

TETRAHEDRON LETTERS, 1984, 25 (46) :5323-5326

[27]

LAROCK RC, 1991, COMPREHENSIV EORGANI, V4, pCH1

[28]

LASS H, 1981, SYNTHESIS-STUTTGART, P958

[29] ONE-STEP SYNTHESIS OF VINYL CARBAMATES CATALYZED BY MONONUCLEAR RUTHENIUM COMPLEXES VIA ADDITION OF CARBON-DIOXIDE AND AMINE TO TERMINAL ALKYNES [J].

MAHE, R ;

DIXNEUF, PH ;

LECOLIER, S .

TETRAHEDRON LETTERS, 1986, 27 (52) :6333-6336

[30] RUTHENIUM COMPLEX CATALYZED SELECTIVE ADDITION OF CARBOXYLIC-ACIDS TO ACETYLENES GIVING ENOL ESTERS [J].

MITSUDO, T ;

HORI, Y ;

YAMAKAWA, Y ;

WATANABE, Y .

TETRAHEDRON LETTERS, 1986, 27 (19) :2125-2126

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