SYNTHESIS OF BASIC SUBSTITUTED 5H-PYRIMIDO[4,5-C]-2-BENZAZEPINES

被引:8
作者
TROSCHUTZ, R
GRUN, L
机构
[1] Institut für Pharmazie und Lebensmittelchemie, Universität Erlangen-Nürnberg, Erlangen, D-91052
关键词
D O I
10.1002/ardp.19933261104
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The potentially CNS-active title compounds 19a-c can be prepared by a nine step synthesis beginning with phthalaldehydic acid. Knoevenagel condensation of 5 with the acetonitriles 2a-g and subsequent reduction with NaBH4 lead to the dihydrocinnamic acid nitriles 3. Only 3a can be cyclized to the 2-benzazepinnitriles 9a,b. Ammonolysis of 9a yields the enaminonitrile 10, which is reacted with the orthoesters 11a-c to the imidic acid esters 12a-c. Ammonolysis leads to the tricycles 16a,b. After transformation of the lactam group in 16 to an imidoyl chloride 17, aminolysis with the amines 18a-c provides the title compounds 19a-c.
引用
收藏
页码:857 / 864
页数:8
相关论文
共 22 条
[1]  
BOISSIER JR, 1965, ARCH INT PHARMACOD T, V158, P212
[2]  
BOURIN M, 1983, ARZNEIMITTELFORSCH, V33-2, P1173
[3]   WITTIG REACTION OF O-FORMYLBENZYLTRIPHENYLPHOSPHONIUM CHLORIDE [J].
BROWN, C ;
SARGENT, MV .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (13) :1818-&
[4]  
CHERMAT R, 1986, J PHARMACOL-PARIS, V17, P348
[5]  
DIEZBARRA E, 1989, SYNTHESIS-STUTTGART, P391
[6]  
DIEZBARRA E, 1990, J CHEM SOC P1, P2589
[7]  
EICHENBERGER E, 1984, ARZNEIMITTEL-FORSCH, V34-1, P110
[8]   PHOTOBROMINATION OF SUBSTITUTED TOLUENES AS A ROUTE TO SUBSTITUTED BENZYL ALCOHOLS AND BENZALDEHYDES [J].
ELIEL, EL ;
RIVARD, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (09) :1252-1256
[9]  
EUGSTER CH, 1963, HELV CHIM ACTA, V57, P543
[10]   SYNTHESIS OF HETEROCYCLIC-COMPOUNDS .13. 2-AMINO-3-BENZYL-3,5-DICYANO-6-METHOXY-4-PHENYL-3,4-DIHYDROPYRIDINES [J].
FUENTES, L ;
LORENTE, A ;
SOTO, JL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (02) :273-276