INTRAMOLECULAR SULFENYLATION USING SULFOXIDES - PREPARATION OF 5H-PYRROLO[1,2-A][3,1]BENZOTHIAZINES

被引:0
|
作者
PICARD, JA [1 ]
CHEN, SW [1 ]
BATES, DK [1 ]
机构
[1] MICHIGAN TECHNOL UNIV,DEPT CHEM,HOUGHTON,MI 49931
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-[2-(Phenylsulfinylmethyl)phenyl]pyrrole (4) undergoes transfer sulfenylation to N-(2-chloromethylphenyl)-2-phenylthiopyrrole (5') presumably via S-phenyl 5H-pyrrolo[1,2-a][3,1]benzothiazonium chloride (7). Depending upon the rigor of the reaction conditions, either N-(2-hydroxymethylphenyl)-2-phenylthiopyrrole (5) or its 5-trifluoroacetyl derivative (6) are obtained when 4 is treated with TFAA in trifluoroacetic acid. N-[2(Methylsulfinylmethyl) aryl]pyrroles (12), when treated with gaseous hydrogen chloride and the resulting sulfonium salts refluxed in dichloroethane, produce substituted 5H-pyrrolo[1,2-a][3,I]benzothiazines (14). 1-Formyl-5H-pyrrolo[1,2-a][3,1]benzothiazines (22) are formed in one step in good yield when sulfoxides (12) are reacted with the Vilsmeier-Haack reagent (DMF/POCl3). No Pummerer rearrangement product is isolated from these reactions.
引用
收藏
页码:1775 / 1789
页数:15
相关论文
共 50 条
  • [21] Synthesis and Reaction Mechanisms for the Construction of Pyrrolo[1,2-a]quinoxalines and Pyrrolo[1,2-a]quinoxalin-4(5H)-ones
    Jiang, Nan
    Yao, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [22] Intramolecular organolithium addition to indol-2(3H)-ones;: an approach to the synthesis of pyrrolo[1,2-a]indoles and pyrido[1,2-a]indoles
    Jones, K
    Storey, JMD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05): : 769 - 774
  • [23] Synthesis of pyrrolo[1,2-a]quinoline and pyrrolo[1,2-b]isoquinoline derivatives via intramolecular acylation
    Zhai, Yingying
    Hou, Guodong
    Yi, Chengxiang
    Wu, Yangang
    Song, Chuanjun
    TETRAHEDRON, 2024, 166
  • [24] SYNTHESIS OF 3H-PYRROLO(1,2-A)BENZIMIDASOLE DERIVATIVES
    ESAYAN, ZV
    TATEVOSY.GT
    MANUCHAR.LA
    ARMYANSKII KHIMICHESKII ZHURNAL, 1972, 25 (04): : 345 - &
  • [25] 9H-PYRROLO[1,2-A]INDOLES
    MAZZOLA, VJ
    BERNADY, KF
    FRANCK, RW
    JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02): : 486 - &
  • [26] INTRAMOLECULAR ADDITION OF A DIOXOLANYL RADICAL TO THE INDOLE NUCLEUS - PREPARATION OF ENANTIOMERICALLY PURE, OXYGENATED PERHYDRO-3H-PYRROLO[1,2-A]INDOLES
    ZIEGLER, FE
    HARRAN, PG
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10): : 2768 - 2773
  • [27] Novel syntheses of hexahydro-1H-pyrrolo[1,2-a]imidazoles and octahydroimidazo[1,2-a]pyridines
    Katritzky, AR
    Qiu, GF
    He, HY
    Yang, BZ
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (12): : 3683 - 3689
  • [28] SYNTHETIC STUDIES ON SUBSTITUTED 9H-PYRROLO[1,2-A]INDOLES AND 2,3-DIHYDRO-1H-PYRROLO[1,2-A]INDOLES
    YAMADA, Y
    HIRATA, T
    MATSUI, M
    TETRAHEDRON LETTERS, 1969, (02) : 101 - &
  • [29] A NEW AND EXPEDITIOUS SYNTHESIS OF 5H-PYRROLO[1,2-B][2]BENZAZEPINE DERIVATIVES
    CORELLI, F
    GAROFALO, A
    MASSA, S
    ARTICO, M
    SYNTHETIC COMMUNICATIONS, 1990, 20 (07) : 973 - 979
  • [30] Copper-promoted direct sulfenylation of C1-H bonds in 4-aryl pyrrolo[1,2-a]quinoxalines
    Ca, Thuy T.
    Le, Khanh T. M.
    Phan, Son N. T.
    Nguyen, Huy H.
    Le, Huy X.
    Phan, Nam T. S.
    Nguyen, Tung T.
    RSC ADVANCES, 2022, 12 (54) : 34831 - 34836