Photocycloaddition of angelicin and its thiinone analogue to 2,3-dimethylbut-2-ene

被引:6
作者
Bethke, J
Jakobs, A
Margaretha, P
机构
[1] UNIV HAMBURG,INST ORGAN CHEM,D-20146 HAMBURG,GERMANY
[2] UNIV LIEGE,INST HETEROCYCL ORGAN CHEM,B-4000 LIEGE,BELGIUM
关键词
coumarin photochemistry; thiocoumarin photochemistry;
D O I
10.1016/S1010-6030(96)04553-4
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
On irradiation (350 nm) in benzene containing 2,3-dimethylbut-2-ene, angelicin (2) and thioangelicin 3 undergo selective cyclobutane formation at the six-membered heterocycle, i.e, at the pyranone and thiinone C=C double bond respectively. (C) 1997 Elsevier Science S.A.
引用
收藏
页码:83 / 84
页数:2
相关论文
共 14 条
[1]   ANGELICINS, ANGULAR ANALOGS OF PSORALENS - CHEMISTRY, PHOTOCHEMICAL, PHOTOBIOLOGICAL AND PHOTOTHERAPEUTIC PROPERTIES [J].
BORDIN, F ;
DALLACQUA, F ;
GUIOTTO, A .
PHARMACOLOGY & THERAPEUTICS, 1991, 52 (03) :331-363
[2]   PHOTOCHEMISTRY OF THE PSORALENS [J].
HEARST, JE .
CHEMICAL RESEARCH IN TOXICOLOGY, 1989, 2 (02) :69-75
[3]   PHOTOBIOLOGICAL ACTIVITY OF SULFUR AND SELENIUM ANALOGS OF PSORALEN [J].
JAKOBS, A ;
PIETTE, J .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 1994, 22 (01) :9-15
[4]   A convenient synthesis of thiopyrano[2,3-e]benzofuran: A new sulfur analogue of angelicin [J].
Jakobs, AE ;
Christiaens, L .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4842-4844
[5]   1-THIOMETHOXSALEN AND 1-THIOPSORALEN - SYNTHESIS, PHOTOBIOLOGICAL PROPERTIES, AND SITE-SPECIFIC REACTION OF THIOPSORALENS WITH DNA [J].
JAKOBS, AE ;
PIETTE, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (06) :869-874
[6]   PHOTOCYCLOADDITIONS TO 1-THIOCOUMARIN [J].
KARBE, C ;
MARGARETHA, P .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 57 (1-3) :231-233
[7]  
Klaus CP, 1996, LIEBIGS ANN, P291
[8]   PHOTOCHEMICAL-REACTION OF FUROCOUMARIN (PSORALEN) - THE REACTIVE SITE IN ITS PHOTOEXCITED STATE [J].
OTSUKI, T .
CHEMISTRY LETTERS, 1987, (03) :453-454
[9]  
Ratiner B. D., 1990, CHEM EXPRESS, V5, P225
[10]   PHOTOCHEMICAL REACTIVITY OF 3-ETHOXYCARBONYLFUROCOUMARIN [J].
RATINER, BD ;
OTSUKI, T .
CHEMISTRY LETTERS, 1989, (06) :1035-1038