SYNTHESIS OF THE CARBAZOLE ALKALOIDS HYELLAZOLE AND 6-CHLOROHYELLAZOLE AND RELATED DERIVATIVES

被引:44
作者
BECCALLI, EM
MARCHESINI, A
PILATI, T
机构
[1] UNIV STUDI MILANO,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
[2] CNR,CTR STUDI RELAZ STRUTTURA & REATTIVITA CHIM,I-20133 MILAN,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 05期
关键词
D O I
10.1039/p19940000579
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe a new seven-stage synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole, which proceeds via thermal cyclization of the 3-(buta-1,3 dienyl)indoles 7ab and 7bb. prepared from the condensation products of indole-2,3-diones 1a, b and the 3-methyl-4-phenylbut-3-en-2-one 2b. This procedure was also used to prepare related 3-methoxy-1-phenylcarbazole derivatives.
引用
收藏
页码:579 / 587
页数:9
相关论文
共 21 条
[1]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[2]   SYNTHESIS AND STEREOCHEMISTRY OF SOME ISATYLIDENEACETIC ACID DERIVATIVES [J].
AUTREY, RL ;
TAHK, FC .
TETRAHEDRON, 1967, 23 (02) :901-&
[3]   SYNTHESIS OF [A]ANNULATED CARBAZOLES FROM INDOL-2,3-DIONE [J].
BECCALLI, EM ;
MARCHESINI, A ;
PILATI, T .
TETRAHEDRON, 1993, 49 (21) :4741-4758
[4]   SYNTHESIS OF CARBAZOLE ALKALOIDS [J].
BERGMAN, J ;
PELCMAN, B .
PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :1967-1976
[5]  
CARDELLINA JH, 1979, TETRAHEDRON LETT, P4915
[6]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[7]   AN ANNULATION METHOD FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED POLYCYCLIC AROMATIC AND HETEROAROMATIC-COMPOUNDS [J].
DANHEISER, RL ;
BRISBOIS, RG ;
KOWALCZYK, JJ ;
MILLER, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3093-3100
[8]  
DORNOW A, 1952, LIEBIGS ANN CHEM, V578, P101
[9]  
FRENZ BA, 1983, ENRAF NONIUS STRUCTU
[10]   On the condensation of methylpropyl ketone with benzaldehyde. [J].
Harries, C ;
Bromberger, P .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1902, 35 :3088-3090