Reaction of 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones with ethyl(triphenylphosphoranylidene) acetate

被引:18
作者
Kafka, S [1 ]
Kovar, M [1 ]
Klasek, A [1 ]
Kappe, T [1 ]
机构
[1] KARL FRANZENS UNIV GRAZ,INST ORGAN CHEM,A-8010 GRAZ,AUSTRIA
关键词
D O I
10.1002/jhet.5570330667
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Wittig reaction of 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones 2 with ethyl (triphenylphosphoranylidene)acetate 3 proceeds stereoselectively to give E-4-carbethoxymethylene-1,2,3,4-tetrahydro-2-quinolones 4, which were hydrolyzed to corresponding acids 6. Butenolides 5 were detected end, in some cases, isolated as a minor product of the Wittig reaction.
引用
收藏
页码:1977 / 1982
页数:6
相关论文
共 50 条
[31]   Reaction of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with nicotinic hydrazide [J].
Baeva, Larisa A. ;
Nugumanov, Radik M. ;
Gataullin, Rail R. ;
Fatykhov, Akhnef A. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (05) :548-554
[32]   A new method for the synthesis of 3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline [J].
Barvainiene, B ;
Stanisauskaite, A ;
Getautis, V .
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (01) :138-139
[33]   ENAMINOKETONES .4. 1,2,3,4-TETRAHYDRO-PYRIDO 2,3-D!-PYRIMIDINE-2,4-DIONES [J].
JUNEK, H ;
WRTILEK, I .
MONATSHEFTE FUR CHEMIE, 1970, 101 (04) :1130-&
[34]   REACTION OF COAL WITH 1,2,3,4- TETRAHYDROQUINOLINE IN A PERFLUOROCARBON MEDIUM [J].
KAUFMAN, M ;
JAMISON, WCL ;
GANDHI, S ;
LIOTTA, D .
FUEL, 1987, 66 (12) :1621-1625
[35]   Ethyl (3-ethyl-1-oxo-1,2,3,4-tetrahydrocarbazol-2-yl)acetate [J].
Kaynak, FB ;
Özbey, S ;
Uludag, N ;
Patir, S .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2004, 60 :O120-O122
[36]   Single-stage synthesis of 3-hydroxy- and 3-alkoxy-5-arylimidazolidine-2,4-diones by reaction of arylglyoxal hydrates with N-hydroxy- and N-alkoxyureas [J].
Vasiliy G. Shtamburg ;
Viktor V. Shtamburg ;
Andrey A. Anishchenko ;
Roman I. Zubatyuk ;
Aleksander V. Mazepa ;
Eugene A. Klotz ;
Svetlana V. Kravchenko ;
Remir G. Kostyanovsky .
Chemistry of Heterocyclic Compounds, 2015, 51 :553-559
[37]   Single-stage synthesis of 3-hydroxy- and 3-alkoxy-5-arylimidazolidine-2,4-diones by reaction of arylglyoxal hydrates with N-hydroxy- and N-alkoxyureas [J].
Shtamburg, Vasiliy G. ;
Shtamburg, Viktor V. ;
Anishchenko, Andrey A. ;
Zubatyuk, Roman I. ;
Mazepa, Aleksander V. ;
Klotz, Eugene A. ;
Kravchenko, Svetlana V. ;
Kostyanovsky, Remir G. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (06) :553-559
[38]   Novel method for synthesis of 3-hydroxy-1-phenyl-1,2,3,4- tetrahydroquinoline [5] [J].
Kaunas University of Technology, Organic Chemistry Department, Kaunas LT-50270, Lithuania .
Chem. Heterocycl. Compd., 2006, 1 (123-124) :123-124
[39]   Methyl 1-benzoyl-3-hydroxy-4-methoxy1,2,3,4-tetrahydroquinoline-2-carboxylate [J].
Evain, M ;
Pauvert, M ;
Collet, S ;
Guingant, A .
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 :O754-O755
[40]   Synthesis and herbicidal evaluation of novel 3-[(α-hydroxy-substituted)benzylidene]pyrrolidine-2,4-diones [J].
Zhu, YQ ;
Zou, XM ;
Hu, FZ ;
Yao, CS ;
Liu, B ;
Yang, HZ .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (24) :9566-9570