SYNTHESIS OF PYRROLOQUINOLINES FROM SUBSTITUTED 6-AMINOINDOLES AND OXALOACETIC ESTER

被引：1

作者：

Yamashkin, S. A. ^{[1
]}

Zhukova, N. V. ^{[1
]}

Romanova, I. S. ^{[1
]}

机构：

[1] M E Evsevyev Mordovinian State Pedag Inst, Saransk 430007, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2008年 / 44卷 / 07期

关键词：

substituted; 6-aminoindoles; pyrrolo[2,3-f]quinolines; pyrrolo[3,2-g]quinolines; oxaloacetic ester;

D O I：

10.1007/s10593-008-0111-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It was established that the initial condensation of substituted 6-aminoindoles and oxaloacetic ester in boiling benzene with the addition of catalytic amounts of acetic acid takes place exclusively through the carboxyl group of the keto ester with the formation of the corresponding enamines, which successfully undergo thermal cyclization (biphenyl, 280 degrees C) to pyrroloquinolines. Here, irrespective of the nature of substituents at the N-1 and C-5 atoms enamines with a free position 7 are transformed into pyrrolo-[2,3-f]quinolines (structural analogs of vitamin PQQ) while 7-OMe-substituted enamines give pyrrolo[3,2-g]quinolines with linear fusion of the rings.

引用

页码：793 / 801

页数：9

共 50 条

[21] SYNTHESIS OF SUBSTITUTED 2-AMINOINDOLES AND 2-(2'-PHENYL-1',3',4'-OXADIAZOLYL)AMINOINDOLES
HIREMATH, SP
MRUTHYUNJAYASWAMY, BHM
PUROHIT, MG
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1978, 16 (09): : 789 - 792
[22] Synthesis of pyrroloquinolines from 2,3-dimethyl-5-methoxy-6-aminoindole
Yamashkin, SA
Kucherenko, NY
Yurovskaya, MA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (07): : 941 - 945
[23] Synthesis of pyrroloquinolines from 2,3-dimethyl-5-methoxy-6-aminoindole
Yamashkin S.A.
Kucherenko N.Ya.
Yurovskaya M.A.
Chemistry of Heterocyclic Compounds, 1997, 33 (7) : 823 - 827
[24] Synthesis of substituted pyrrolo[3,2-f]-quinolines from 5-aminoindoles and diethyl oxaloacetate
Yamashkin S.A.
Zhukova N.V.
Romanova N.S.
Chem. Heterocycl. Compd., 2007, 1 (67-75): : 67 - 75
[25] STERIC EFFECTS AT SYNTHESIS OF PYRROLOINDOLES FROM 5-AMINOINDOLES
YAMASHKIN, SA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1995, (01): : 55 - 57
[26] Formation of Pyrrolo[2,3-f]Quinolines from Substituted 5-Methyl-6-aminoindoles by the Combes Reaction
Yamashkin, S. A.
Kucherenko, N. Y.
Yurovskaya, M. A.
Chemistry of Heterocyclic Compounds, 1995, 31 (11)
[27] 2,3-dimethyl-7-methoxy-6-aminoindole in synthesis of linear pyrroloquinolines
Yamashkin, SA
Kucherenko, NY
Yurovskaya, MA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (01): : 75 - 79
[28] 2,3-Dimethyl-7-methoxy-6-aminoindole in the synthesis of linear pyrroloquinolines
Chem. Heterocycl. Compd., 1 (64-68):
[29] 2,3-Dimethyl-7-methoxy-6-aminoindole in the synthesis of linear pyrroloquinolines
Yamashkin S.A.
Kucherenko N.Ya.
Yurovskaya M.A.
Chemistry of Heterocyclic Compounds, 1997, 33 (1) : 64 - 68
[30] A Practical Route to Substituted 7-Aminoindoles from Pyrrole-3-carboxaldehydes
Outlaw, Victor K.
Townsend, Craig A.
ORGANIC LETTERS, 2014, 16 (24) : 6334 - 6337

← 1 2 3 4 5 →