New syntheses of pyrrolo[3,4-b]indoles, benzo[b]furo[2,3-c]pyrroles, and benzo[b]thieno [2,3-c]pyrroles utilizing the reaction of munchnones (1,3-oxazolium-5-olates) with nitroheterocycles

被引：0
|
作者：
Gribble, GW [1 ]
Pelkey, ET [1 ]
Switzer, FL [1 ]
机构：
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
来源：
SYNLETT | 1998年 / 10期
关键词：
munchnones; nitroheterocycles; 1,3-dipolar cycloaddition; pyrrolo[3; H-b]indoles; fused pyrroles;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of munchnones (mesoionic 1,3-oxazolium-5-olates) 3 and 4 with 2- and 3-nitroindoles, 2-nitrobenzo[b]furan, and 3-nitrobenzo[b]thiophene affords the corresponding pyrrolo[3,4-b]indoles, benzo[b]furo[2,3-c]pyrroles, and benzo[b]thieno[2,3-c]pyrroles, respectively, in one operation in good to excellent yields.
引用
收藏
页码：1061 / +
页数：3
相关论文
共 50 条
  • [1] A novel class of fused heterocycles, benzo[b]furo[2,3-c]pyrroles
    Trujillo, HA
    Simon, WM
    Pelkey, ET
    Gribble, GW
    Jasinski, JP
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2000, 56 : 386 - 388
  • [2] CONDENSED PYRIDINE BASES - SYNTHESIS OF SOME DERIVATIVES OF BENZO[B]FURO[2,3-C]QUINOLINE, BENZO[B]THIENO[2,3-C]QUINOLINE AND BENZO[B]SELENOPHENO[2,3-C]QUINOLINE
    TOLKUNOV, SV
    KHIZHAN, AI
    SIMONOVA, SI
    SEMENOV, NS
    LYASHCHUK, SN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (03): : 321 - 326
  • [3] SYNTHESIS AND REACTIONS OF BENZO[B]FURO[2,3-C]PYRYLIUM SALTS
    DULENKO, VI
    TOLKUNOV, SV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (07): : 889 - 893
  • [4] AMINO-THIENO[2,3-C]PYRAZOLES AND AMINO-THIENO[2,3-B]PYRROLES
    GEWALD, K
    RENNERT, S
    SCHINDLER, R
    SCHAFER, H
    JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1995, 337 (06): : 472 - 477
  • [5] ELECTROPHILIC SUBSTITUTION IN BENZO[B]THIENO[2,3-C]PYRIDINES - NITRATION
    TOLKUNOV, SV
    KALNITSKY, MN
    DULENKO, VI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1993, (05): : 706 - 709
  • [6] SYNTHESIS AND REACTIONS OF BENZO[B]THIENO[2,3-C]PYRILIUM SALTS
    DULENKO, VI
    TOLKUNOV, SV
    ALEKSEYEV, NN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1981, (10): : 1351 - 1354
  • [7] ELECTROPHILIC SUBSTITUTION IN BENZO[B]THIENO[2,3-C]PYRIDINES - ACYLATION
    TOLKUNOV, SV
    KALNITSKY, MN
    LYASHCHUK, SN
    DULENKO, VI
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1994, (05): : 701 - 705
  • [8] 2 NEW PROCESSES FOR THE SYNTHESIS OF BENZO(B)THIENO(3,2-C) AND (2,3-C)PYRIDINES
    FREHEL, D
    MAFFRAND, JP
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1979, 6 (1-2): : 97 - 97
  • [9] SYNTHESIS OF 3-AMINO DERIVATIVES OF BENZO[B]FURO[2,3-C]PYRIDINES
    TOLKUNOV, SV
    KALNITSKY, MN
    ZEMSKAYA, EA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (11): : 1552 - 1555
  • [10] Electrophilic substitution in benzo[b]furo[2,3-c]pyridines: Nitration, acylation
    Tolkunov, S.V.
    Kal'Nitskii, M.N.
    Dulenko, V.I.
    Lyashchuk, S.N.
    Chemistry of Heterocyclic Compounds, 1995, 31 (05) : 615 - 620
12345