Synthesis and reactivity of α-halogenated, C-protected β-enamino acids

被引:3
作者
Fustero, S [1 ]
Salavert, E [1 ]
Sanz-Cervera, JF [1 ]
Román, R [1 ]
Fernández-Gutiérrez, BF [1 ]
Asensio, A [1 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain
关键词
halogenation; beta-enamino acid; uracil; oxazoline;
D O I
10.2174/1570178043488545
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-Protected beta-enamino acids (I) reacted with one equivalent of N-halosuccinimides (NXS) to furnish their alpha-halogenated derivatives (II). These compounds were then successfully transformed into halogenated Uracil derivatives (III) through reaction with triphosgene. followed by 5-membered ring-opening under acidic conditions.
引用
收藏
页码:163 / 167
页数:5
相关论文
共 40 条
[1]   CYANOGEN-BROMIDE AS A USEFUL BROMINATING AGENT - SYNTHESIS OF ALPHA-BROMO-BETA-AMINOENONES [J].
ALBEROLA, A ;
ANDRES, C ;
ORTEGA, AG ;
PEDROSA, R ;
VICENTE, M .
SYNTHETIC COMMUNICATIONS, 1986, 16 (10) :1161-1165
[2]   A USEFUL SYNTHESIS OF 3-HALOGENO-1-AZABUTADIENE DERIVATIVES, AND THEIR APPLICABILITY IN THE PREPARATION OF HETEROCYCLES [J].
BARLUENGA, J ;
TOMAS, M ;
LOPEZORTIZ, JF ;
GOTOR, V .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2273-2276
[3]  
Blaise EE, 1901, CR HEBD ACAD SCI, V132, P978
[4]  
Braibante MEF, 2001, SYNTHESIS-STUTTGART, P1935
[5]  
CAMPOS PJ, 1995, TETRAHEDRON LETT, V36, P5257
[6]   THE PREPARATION OF BETA-KETO ESTERS FROM NITRILES AND ALPHA-BROMOESTERS [J].
CASON, J ;
RINEHART, KL ;
THORNTON, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (11) :1594-1600
[7]  
Chu C.K., 1993, Nucleosides and Nucleotides as Antitumor and Antiviral Agents
[8]  
Cotarca L, 1996, SYNTHESIS-STUTTGART, P553
[9]   THE SYNTHESIS OF BETA-HALOGENATED ENAMINES [J].
DEKIMPE, N ;
SCHAMP, N .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1981, 13 (3-4) :241-313
[10]  
DEKIMPE N, 1979, ORG PREP PROCED INT, V11, P115