TETRAPYRROLES .4. A HIGHLY EFFICIENT SYNTHESIS OF HOMOCHIRAL DIHYDROPYRROMETHENONES VIA PD(0) MEDIATED COUPLING OF IODOPYRROLES AND ACETYLENIC AMIDES

被引:20
作者
JACOBI, PA
RAJESWARI, S
机构
[1] Hall-Atwater Laboratories, Wesleyan University, Middletown
关键词
PHYTOCHROME; DIHYDROPYRROMETHENONES; IODOPYRROLES; PD(0)COUPLING; ACETYLENIC AMIDES;
D O I
10.1016/S0040-4039(00)60941-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homochiral dihydropyrromethenones of type 20 have been synthesized in a highly efficient manner by Pd(o) mediated coupling of iodopyrrole 14 with acetylenic amides 18, followed by F- catalyzed 5-exo-dig cyclization. In analogous fashion, phytochrome (8) precursor 25a has been prepared in 85% overall yield from iodopyrrole 22.
引用
收藏
页码:6235 / 6238
页数:4
相关论文
共 20 条
[1]   SYNTHESIS OF 3-ARYLPYRROLES AND 3-PYRROLYLACETYLENES BY PALLADIUM-CATALYZED COUPLING REACTIONS [J].
ALVAREZ, A ;
GUZMAN, A ;
RUIZ, A ;
VELARDE, E ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1653-1656
[2]  
BARTON DHR, 1990, TETRAHEDRON, V46, P7587
[3]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[4]  
CHEN W, 1990, THESIS U ALABAMA TUS
[5]   PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].
DIECK, HA ;
HECK, FR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263
[6]   CATALYST TAILORING FOR PALLADIUM-MEDIATED CROSS COUPLING OF ARYLSTANNANES WITH VINYL TRIFLATES [J].
FARINA, V ;
ROTH, GP .
TETRAHEDRON LETTERS, 1991, 32 (34) :4243-4246
[7]   TETRAPYRROLES .3. HOMOCHIRAL DIHYDROPYRROMETHENONES FROM N-AMINOPYRROLES AND ACETYLENIC ACIDS [J].
JACOBI, PA ;
RAJESWARI, S .
TETRAHEDRON LETTERS, 1992, 33 (42) :6231-6234
[8]   2-OXO-3-BUTENOATE ESTERS AS DIENOPHILES AND THEIR UTILITY IN A NOVEL SYNTHESIS OF PYRROLES [J].
JACOBI, PA ;
CAI, GL .
TETRAHEDRON LETTERS, 1991, 32 (15) :1765-1768
[9]  
MAGNUS, 1992, J AM CHEM SOC, V114, P2544
[10]  
NICHOLAS KM, 1978, TRANSITION METAL ORG, V2