Application of modified Pictet-Spengler reaction for the synthesis of thiazolo- and pyrazolo-quinolines

被引：64

作者：

Duggineni, S ^{[1
]}

Sawant, D ^{[1
]}

Saha, B ^{[1
]}

Kundu, B ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med Chem, Lucknow 226014, Uttar Pradesh, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 14期

关键词：

thiazoloquinoline; pyrazoloquinoline; Pictet-Spengler reaction; C-C bond formation;

D O I：

10.1016/j.tet.2006.01.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new thiazole and pyrazole-based arylamine substrate have been used for the Pictet-Spengler reaction. This is in contrast to the traditionally used indole/imidazole-based aliphatic amine substrates that has remained in use for the last similar to 100 years. The condensation of both the substrates with a variety of aldehydes in the presence of 2% TFA-DCM at 0 degrees for 30 min or pTsOH in toluene at reflux led to the synthesis of thiazoloquinolines and pyrazoloquinolines, respectively. Unlike aliphatic amine substrates, our substrates readily underwent Pictet-Spengler cyclization even with aldehydes having electron donating group. The studies are based on a new concept proposed by us that arylamines linked to an activated heterocyclic ring can lead to a variety of second-generation substrates for the Pictet-Spengler cyclization. Our studies open up new avenues for the application of Pictet-Spengler reaction beyond syntheses of the tetrahydroisoquinolines and tetrahydro-beta-carbolines. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3228 / 3241

页数：14

共 89 条

[1] Synthesis and antitumor evaluation of new thiazolo[5,4-b]quinoline derivatives
AlvarezIbarra, C
FernandezGranda, R
Quiroga, ML
Carbonell, A
Cardenas, F
Giralt, E
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (05) : 668 - 676
[2] New potent and selective human adenosine A3 receptor antagonists
Baraldi, PG
Borea, PA
[J]. TRENDS IN PHARMACOLOGICAL SCIENCES, 2000, 21 (12) : 456 - 459
[3] Chemistry of secologanin,: part 10.: Investigation of Pictet-Spengler type reactions of secologanin with histamine and its benzyl derivative
Beke, G
Szabó, LF
Podányi, B
[J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (05): : 649 - 655
[4] LACK OF TOLERANCE OR WITHDRAWAL EFFECTS IN MICE AFTER CHRONIC ADMINISTRATION OF THE NONSEDATING ANXIOLYTIC, CGS-9896
BOAST, CA
GERHARDT, SC
[J]. PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1987, 26 (03) : 601 - 606
[5] Solid-phase synthesis of tetrahydro-β-carbolinehydantoins via the N-acyliminium Pictet-Spengler reaction and cyclative cleavage
Bonnet, D
Ganesan, A
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (06): : 546 - 548
[6] Tricyclic heteroaromatic systems. Pyrazolo[3,4-c]quinolin-4-ones and pyrazolo[3,4-c]quinoline-1,4-diones: Synthesis and benzodiazepine receptor activity
Catarzi, D
Colotta, V
Varano, F
Cecchi, L
Filacchioni, G
Galli, A
Costagli, C
[J]. ARCHIV DER PHARMAZIE, 1997, 330 (12) : 383 - 386
[7] Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases - a solution-phase strategy for library synthesis
Chang, JB
Zhao, K
Pan, SF
[J]. TETRAHEDRON LETTERS, 2002, 43 (06) : 951 - 954
[8] FOOD PALATABILITY AND HUNGER MODULATED EFFECTS OF CGS-9896 AND CGS-8216 ON FOOD-INTAKE
CHEN, SW
DAVIES, MF
LOEW, GH
[J]. PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1995, 51 (2-3) : 499 - 503
[9] Synthesis and structure-activity relationships of a new set of 2-arylpyrazolo[3,4-c] quinoline derivatives as adenosine receptor antagonists
Colotta, V
Catarzi, D
Varano, F
Cecchi, L
Filacchioni, G
Martini, C
Trincavelli, L
Lucacchini, A
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (16) : 3118 - 3124
[10] Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify an optional binding site of a benzodiazepine receptor ligand
Colotta, V
Catarzi, D
Varano, F
Filacchioni, G
Cecchi, L
Galli, A
Costagli, C
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (15) : 2915 - 2921

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