Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]-indol-2-one derivatives with aromatic aldehydes

被引：0

作者：

Sackus A. ^{[1
]}

Amankaviciene V. ^{[1
]}

机构：

[1] Department of Organic Chemistry, Faculty of Chemical Technology, Kaunas University of Technology

来源：

Chemistry of Heterocyclic Compounds | 2002年 / 38卷 / 07期

关键词：

1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one; 9a-(2-phenylethenyl)-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one; Alkylation; Condensation;

D O I：

10.1023/A:1020685704961

中图分类号：

学科分类号：

摘要：

Condensation of 1-alkyl-, 1-allyl-, and 1-benzyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones with benzaldehydes in acetic acid and subsequent treatment of the reaction mixture with potassium hydroxide afforded 1-substituted 9a-(2-phenylethenyl)-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one derivatives. 1-Methyl- and 1-ethyl-9a-[2-(4-dimethylaminophenyl)ethenyl]-1,2,3,9a-tetrahydro-9H-imidazo [1,2-a]indol-2-ones were synthesized by alkylation of 9a-[2-(4-dimethylaminophenyl)ethenyl]-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a] indol-2-one with methyl- and ethyl iodides in DMF in the presence of a strong base.

引用

页码：822 / 827

页数：5

共 50 条

[1] Condensation of 1-substituted 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one derivatives with aromatic aldehydes
Sackus, A
Amankaviciene, V
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (07): : 931 - 936
[2] ALKYLATION OF 1,2,3,9A-TETRAHYDRO-9H-IMIDAZO[1,2-A]INDOL-2-ONE DERIVATIVES
SHACHKUS, AA
DEGUTIS, YA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1988, (01): : 49 - 53
[3] 1,2,3,9A-TETRAHYDRO-9H-IMIDAZO[1,2-A]INDOLES
DEGULIS, YA
SHACHKUS, AA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (02): : 227 - 230
[4] SYNTHESIS OF 1-SUBSTITUTED 1,2,3,9-ALPHA-TETRAHYDRO-9H-IMIDAZO[1,2-ALPHA]INDOL-2-ONES
SHACHKUS, AA
DEGUTIS, YA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (11): : 1485 - 1489
[5] INTERACTION OF 2,3,3-TRIMETHYL-3H-INDOLE WITH HALOACETAMIDES - SYNTHESIS OF 1,2,3,9A-TETRAHYDRO-9H-IMIDAZO[1,2-A]INDOL-2-ONES
DEGUTIS, YA
SHACHKUS, AA
URBONAVICHYUS, AG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1985, (07): : 933 - 935
[6] Synthesis of 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]-indol-2-ones by reaction of 2,3,3-trimethyl-3H-indole with 2-bromopropionamides
E. Valaityte
V. Martynaitis
A. Sackus
Chemistry of Heterocyclic Compounds, 2004, 40 (11) : 1460 - 1464
[7] Synthesis of 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9h-imidazo[1,2-a]-indol-2-ones by reaction of 2,3,3-trimethyl-3h-indole with 2-bromopropionamides
E. Valaityte
V. Martynaitis
A. Sackus
Chemistry of Heterocyclic Compounds, 2004, 40 (11) : 1460 - 1464
[8] Synthesis of 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-ones by reaction of 2,3,3-trimethyl-3H-indole with 2-bromopropionamides
Valaityte, E
Martynaitis, V
Sackus, A
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (11): : 1690 - 1694
[9] Synthesis of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indole2-thione and 1,5,6,10b-tetrahydroimidazo[2,1-a]isoquinoline-2(3H)-thione derivatives
Valaityte, E
Martynaitis, V
Sackus, A
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2004, (11): : 1695 - 1700
[10] Synthesis of 1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indole-2-thione and 1,5,6,10b-tetrahydroimidazo[2,1-a]-isoquinoline-2(3H)-thione derivatives
Valaityte, E.
Martynaitis, V.
Sackus, A.
Chemistry of Heterocyclic Compounds, 2004, 40 (11) : 1465 - 1469

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