Ring-ring interconversions.: Part 2.: Effect of the substituent on the rearrangement of 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles into 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c][1,2,4]oxadiazol-3-ones.: A novel class of potential antitumor agents

被引：14
|
作者：
Billi, R
Cosimelli, B
Spinelli, D
Rambaldi, M
机构：
[1] Dipartimento Chim Organ A Mangini, I-40127 Bologna, Italy
[2] Univ Bologna, Dipartimento Sci Farmaceut, I-40126 Bologna, Italy
来源：
TETRAHEDRON | 1999年 / 55卷 / 17期
关键词：
D O I：
10.1016/S0040-4020(99)00189-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of several 6-aryl-3-methyl-5-nitrosoimidazo[2,1-b][1,3]thiazoles with hydrochloric acid by refluxing in ethanol gives new 8-aryl-8-hydroxy-5-methyl-8H-[1,4]thiazino[3,4-c] [1,2,4]oxadiazol-3-ones for testing of their biological activity. By carrying out the reaction at room temperature it has been possible to isolate reaction intermediates to which structures have been assigned. This study has provided information on the reaction mechanism and on the effect of the substituent in the phenyl ring on the yield of the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5433 / 5440
页数：8
相关论文
共 50 条
  • [41] Investigations on the synthesis and pharmacological properties of 4-alkoxy-2-[2-hydroxy-3-(4-aryl-1-piperazinyl)propyl]-6-methyl-1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones
    Sladowska, H
    Filipek, B
    Szkatula, D
    Sabiniarz, A
    Kardasz, M
    Potoczek, J
    Sieklucka-Dziuba, M
    Rajtar, G
    Kleinrok, Z
    Lis, T
    FARMACO, 2002, 57 (11): : 897 - 908
  • [42] Novel preparation of 1-aryl-3-(2-hydroxyphenyl)-2-pyrazolin-5-ones and their conversion into 2-aryl-4-methyl[1]benzopyrano[4,3-c]pyrazol-3(2H)-ones
    Froggett, JA
    Hockley, MH
    Titman, RB
    JOURNAL OF CHEMICAL RESEARCH-S, 1997, (01): : 30 - 31
  • [43] An efficient synthesis of novel 3′-substituted 2-aryl-5-methyl-5′thioxo-[4,4′-bi-4H-1,2,4-triazol]-3(1′H, 2H)-ones
    Kamble, Ravindra R.
    Sudha, Belgur S.
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (04) : 331 - 337
  • [44] SYNTHESIS OF NOVEL FLUORINE-CONTAINING TETRACYCLIC RING-SYSTEMS - 2-METHYL-1-OXO-11H-1,2,4-TRIAZINO [3',4'-3,4][1,2,4] TRIAZINO [5,6-B] INDOLE AND 3-METHYL-4-OXO-11H-1,2,4-TRIAZINO [4',3'-2,3][1,2,4] TRIAZINO [5,6-B] INDOLE
    JOSHI, KC
    CHAND, P
    DANDIA, A
    AHMED, N
    JOURNAL OF FLUORINE CHEMISTRY, 1987, 35 (01) : 254 - 254
  • [45] Synthesis of derivatives of pyrano[3,4-c][1,2,4]triazolo[4,3-a]pyridine and 8-(pyrazol-1-yl)pyrano[3,4-c]pyridine through pyridine ring rearrangement
    Paronikyan, Ervand G.
    Dashyan, Shushanik Sh.
    Minasyan, Nune S.
    Stepanyan, Grachya M.
    Ayvazyan, Armen G.
    Tamazyan, Rafael A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (12) : 1078 - 1086
  • [46] SYNTHESIS OF PYRROLO[3,4-E][1,4]DIAZEPINE DERIVATIVES .1. 2,3-DIHYDRO-5-ARYL-7-ARYL-PYRROLO[3,4-E][1,4] DIAZEPINE-6-THIOXO-8-(1H,7H)-ONES
    ZANKOWSKAJASINSKA, W
    BOROWIEC, H
    BURGIEL, M
    GOLUS, J
    GORALIK, W
    KOLASA, A
    POLISH JOURNAL OF CHEMISTRY, 1985, 59 (02) : 159 - 167
  • [47] Synthesis of 4-amino-6-R-4,5-dihydro-3-phenacylthio-1,2,4-triazin-5-ones and 8H-3-R-7-aryl-1,2,4-triazino[3,4-b][1,3,4]thiadiazin-4-ones
    Bazavova, IN
    Britsun, VN
    Esipenko, AN
    Lozynskii, MO
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (06): : 937 - 940
  • [48] Synthesis of 4-Amino-6-R-4,5-dihydro-3-phenacylthio-1,2,4-triazin-5-ones and 8H-3-R-7-Aryl-1,2,4-triazino[3,4-b][1,3,4]thiadiazin-4-ones
    I. M. Bazavova
    V. N. Britsun
    A. N. Esipenko
    M. O. Lozinskii
    Chemistry of Heterocyclic Compounds, 2003, 39 (6) : 809 - 812
  • [49] 5 ''-(2-Fluorobenzylidene)-1 '-(2-fluorophenyl)-1 ''-methyl-1 ',2 ',3 ',5 ',6 ',7 ',8 ',8a '-octahydrodispiro[acenaphthylene-1,3 '-indolizine-2 ',3 ''-piperidine]- 2,4 ''(1H)-dione
    Vishnupriya, R.
    Suresh, J.
    Sivakumar, S.
    Kumar, R. Ranjith
    Lakshman, P. L. Nilantha
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1291 - +
  • [50] SYNTHESIS OF 4-SUBSTITUTED 8-AMINO-4,5-DIHYDRO-3H-PYRROLO[3,4-F]-1,3,5-TRIAZEPIN-6-ONES AND 5-AMINO-2-ARYL-4-(1-ARYL-5-ALKYLIDENEAMINOIMIDAZOL-4-YL)1,3-OXAZOLES
    ALVES, MJ
    ALDUAIJ, OK
    BOOTH, BL
    CARVALHO, A
    EASTWOOD, PR
    FERNANDA, M
    PROENCA, JRP
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (24): : 3571 - 3577
12345