HETEROCYCLES WITH A BENZOTHIADIAZEPINE MOIETY .4. SYNTHESIS OF NOVEL TETRACYCLIC RINGS BY INTRAMOLECULAR CYCLIZATION OF 10-BROMOACETYL-10,11-DIHYDRO-11-ETHOXYCARBONYLPYRROLO[1,2-B] [1,2,5] BENZOTHIADIAZEPINE 5,5-DIOXIDE AND ITS DERIVATIVES

被引:15
作者
SILVESTRI, R
PAGNOZZI, E
STEFANCICH, G
ARTICO, M
机构
[1] UNIV ROMA LA SAPIENZA,DIPARTIMENTO STUDI FARMACEUT,P A MORO 5,I-00185 ROME,ITALY
[2] UNIV TRIESTE,DIPARTIMENTO SCI FARMACEUT,I-34127 TRIESTE,ITALY
关键词
D O I
10.1080/00397919408010583
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel tetracyclic derivatives, namely 5 and 8, have been synthesized by intramolecular cyclization of the 10-bromoacetyl-10,11-dihydro-11-ethoxycarbonylpyrrolo[1,2-b] [ 1,2,5]benzothiadiazepine 5,5-dioxide (3) and, respectively, the bis-methylamide of 11-carboxy-10,11-dihydropyrrolo[1,2-b] [1,2,5]benzothiadiazepine-11-acetic acid 5,5-dioxide (4). The last compound formed when treating with an excess of methylamine either the lactam 5 or the diethyl ester of 11-carboxy-10,11-dihydropyrrolo[1,2-b] [1,2,5]benzothiadiazepine-11-acetic acid 5,5-dioxide (7). An unambiguous synthesis of the diester 7 was achieved to confirm the chemical structure of derivatives 4 and 5.
引用
收藏
页码:2685 / 2695
页数:11
相关论文
共 10 条
  • [1] Ankier S I, 1986, Prog Med Chem, V23, P121, DOI 10.1016/S0079-6468(08)70342-4
  • [2] ARTICO M, 1992, J HETEROCYCLIC CHEM, V29, P1851
  • [3] CHIMENTI F, 1974, FARMACO-ED SCI, V29, P589
  • [4] SYNTHESIS OF PYRAZOLE ANALOGS OF ISOAPTAZEPINE
    MASSA, S
    ARTICO, M
    MAI, A
    MANCUSO, A
    CORELLI, F
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (07) : 1851 - 1854
  • [5] PYRROLOBENZODIAZEPINES AND RELATED SYSTEMS .2. SYNTHESIS AND BIOLOGICAL PROPERTIES OF ISONORAPTAZEPINE DERIVATIVES
    MASSA, S
    ARTICO, M
    MAI, A
    CORELLI, F
    BOTTA, M
    TAFI, A
    PANTALEONI, GC
    GIORGI, R
    COPPOLINO, MF
    CAGNOTTO, A
    SKORUPSKA, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (24) : 4533 - 4541
  • [6] SYNTHESIS OF A NEW TETRACYCLIC SYSTEM RELATED TO APTAZAPINE (CGS-7525A) BY ONE-POT DOUBLE ANNELATION
    MASSA, S
    MAI, A
    CORELLI, F
    [J]. TETRAHEDRON LETTERS, 1988, 29 (49) : 6471 - 6474
  • [7] SYNTHESES OF 3B,4,6,7-TETRAHYDRO-5H,9H-PYRAZINO[2,1-C]PYRROLO[1,2-A][1,4]BENZODIAZEPINE, A VALUABLE PRECURSOR OF POTENTIAL CENTRAL NERVOUS-SYSTEM AGENTS
    MASSA, S
    MAI, A
    ARTICO, M
    CORELLI, F
    BOTTA, M
    [J]. TETRAHEDRON, 1989, 45 (09) : 2763 - 2772
  • [9] STEFANCICH G, 1992, FARMACO, V47, P987
  • [10] STEFANCICH G, UNPUB J HETEROCYCLIC