Synthesis of substituted 3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine as new scaffolds for potential bioactive compounds

被引：9
|
作者：
Henry, N
Sánchez, I
Sabatié, A
Bénéteau, V
Guillaumet, G [1 ]
Pujol, MD
机构：
[1] Univ Orleans, Inst Chim Organ & Analyt, UMR 6005, F-45067 Orleans, France
[2] Univ Barcelona, Fac Farm, CSIC, Unitat Associada,Lab Quim Farmaceut, E-08028 Barcelona, Spain
来源：
TETRAHEDRON | 2006年 / 62卷 / 10期
关键词：
pyrido-oxazines; alpha-halocarbonyl compounds; protected; 2-aminopyridine;
D O I：
10.1016/j.tet.2005.11.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title compounds having different substituents on the heterocyclic framework were prepared by several methods from 2-acetamido-3-hydroxypyridine. The condensation of 2-protected-amino-3-hydroxypyridine with 2-chloroacrylonitrile or ethyl 2,3-dibromopropionate provided in several cases two isomeric pyrido-oxazines. Whereas the reaction of 2-acetamido-3-hydroxypyridine with methyl 2,3-dibromopropionate or with alpha-halocarbonyl compounds gave exclusively the 2-substituted pyrido-oxazine, in a one-step operation. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2405 / 2412
页数：8
相关论文
共 50 条
  • [1] REACTIONS OF 3,4-DIHYDRO-2H-PYRIDO[3,2-B]-1,4-OXAZINES
    CLAUSONKAAS, N
    LEI, J
    HEIDE, H
    ACTA CHEMICA SCANDINAVICA, 1971, 25 (08): : 3135 - +
  • [2] STUDIES ON PYRIDINOL DERIVATIVES .4. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 3,4-DIHYDRO-2H-PYRIDO[3,2-B]-1,4-OXAZINE DERIVATIVES
    TAKEDA, H
    HISAMICHI, K
    FUJITA, H
    MUROGA, S
    SUZUKI, S
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1983, 103 (05): : 497 - 507
  • [3] The first enantioselective synthesis of 4-acety1-3(R)- and 3(S)-(hydroxymethyl)-3,4-dihydro-2H-pyrido[3,2-b]oxazine
    Henry, N
    Guillaumet, G
    Pujol, MD
    TETRAHEDRON LETTERS, 2004, 45 (07) : 1465 - 1468
  • [4] STUDIES ON PYRIDINOL DERIVATIVES .9. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 4-PHENYLALKYL-3,4-DIHYDRO-2H-PYRIDO[3,2-B]-1,4-OXAZINE DERIVATIVES
    TAKEDA, H
    MUROGA, S
    FUJITA, H
    HISAMICHI, K
    SUZUKI, S
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1983, 103 (08): : 857 - 866
  • [5] STUDIES ON PYRIDINOL DERIVATIVES .10. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 4-ACYL-3,4-DIHYDRO-2H-PYRIDO[3,2-B]-1,4-OXAZINE DERIVATIVES
    TAKEDA, H
    HISAMICHI, K
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1983, 103 (12): : 1247 - 1256
  • [6] Synthesis of 4H-pyrido[3,2-b][1,4]oxazine and 3-substituted-4H-pyrido[3,2-b][1,4]oxazines via palladium-catalysed reactions
    Lepifre, F
    Buon, C
    Bouyssou, P
    Coudert, G
    HETEROCYCLIC COMMUNICATIONS, 2000, 6 (05) : 397 - 402
  • [7] STUDIES ON PYRIDINOL DERIVATIVES .7. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF 4-(2-DIALKYLAMINO-1-PHENYLETHYL)-3,4-DIHYDRO-2H-PYRIDO[3,2-B]-1,4-OXAZINE DERIVATIVES
    TAKEDA, H
    MUROGA, S
    FUJITA, H
    HISAMICHI, K
    SUZUKI, S
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1983, 103 (08): : 835 - 848
  • [8] A NEW SYNTHESIS OF PYRIDO[3,2-B][1,4]BENZOTHIAZINES
    MCCARTHY, ET
    TYNDALL, DV
    MEEGAN, MJ
    JOURNAL OF CHEMICAL RESEARCH-S, 1988, (05): : 145 - 145
  • [9] Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines
    Starosotnikov, A. M.
    Ivanova, V. V.
    Klimova, T. A.
    Kolotyrkina, N. G.
    Bastrakov, M. A.
    RUSSIAN CHEMICAL BULLETIN, 2022, 71 (01) : 126 - 130
  • [10] Synthesis of new pyrido[3,2-b][1,4]benzoxazines and -benzothiazines
    A. M. Starosotnikov
    V. V. Ivanova
    T. A. Klimova
    N. G. Kolotyrkina
    M. A. Bastrakov
    Russian Chemical Bulletin, 2022, 71 : 126 - 130
12345