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1.
S. A. Yamashkin E. A. Oreshkina I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2006,42(1):86-91
The reaction of 6-amino-2,3-dimethyl-and 6-amino-1,2,3-trimethyl-5-methoxy(methyl)indoles with 4,4,4-trifluoroacetoacetic
ester and of 6-amino-5-methoxy-1,2,3-trimethylindole also with other β-dicarbonyl compounds has been studied. It was found
that all of the amines investigated undergo condensation readily to form the corresponding enamines while the possible subsequent
cyclization to give pyrrolo[2,3-f]quinolines was found only for the condensation product of 6-amino-2,3,5-trimethylindole
with 4,4,4-trifluoroacetoacetic ester.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp 97–103, January, 2006. 相似文献
2.
S. A. Yamashkin E. A. Oreshkina N. V. Zhukova 《Chemistry of Heterocyclic Compounds》2007,43(8):1044-1051
A study was carried out on the reactions of 4-amino-2,3-dimethyl-and 4-amino-1,2,3-trimethylindoles with acetylacetone, dibenzoylmethane,
ethyl acetoacetate, ethyl trifluoroacetoacetate, and ethyl oxaloacetate. Methods were developed for the synthesis of a series
of substituted pyrrolo-[2,3-h]quinolines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1234–1242, August, 2007. 相似文献
3.
S. A. Yamashkin G. A. Romanova I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2003,39(9):1188-1196
The behavior of 5-amino-2-phenyl- and 5-amino-1-methyl-2-phenylindoles in reactions with acetoacetic, trifluoroacetoacetic, and ethoxymethylenemalonic esters, leading to the preparation of pyrrolo[2,3-g]- and pyrrolo[3,2-f]quinolines with functional substituents has been studied. 相似文献
4.
S. A. Yamashkin G. A. Romanova I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2003,39(8):1048-1056
Methods have been developed for the preparation of several functionally substituted pyrrolo[3,2-h]quinolines via the reaction of 2,3-dimethyl- and 1,2,3-trimethyl-7-aminoindoles with acetoacetic, trifluoroacetoacetic, and ethoxymethylenemalonic esters. 相似文献
5.
S. A. Yamashkin E. A. Oreshkina I. S. Romanova M. A. Yurovskaya 《Chemistry of Heterocyclic Compounds》2005,41(10):1280-1289
The comparative reactivities of 6-amino-1,2,3-trimethyl- and 6-amino-7-methoxy-2,3-dimethylindoles with acetylacetone, dibenzoylmethane,
and with aceto- and trifluoroacetoacetic esters have been studied. Methods have been developed for the preparation of some
functionally substituted pyrrolo-[3,2-g]quinolines.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1529–1539, October, 2005. 相似文献
6.
Subburethinam RameshRajagopal Nagarajan 《Tetrahedron letters》2011,52(38):4857-4860
An efficient and convenient one-pot intramolecular aza Diels-Alder approach for the synthesis of dihydrochromeno[4,3-b]pyrrolo[3,2-f]quinolines has been reported. Particularly valuable features of this methodology include simple execution, inexpensive catalyst, and good product yields. 相似文献
7.
S. A. Yamashkin N. V. Zhukova I. S. Romanova 《Chemistry of Heterocyclic Compounds》2008,44(7):793-801
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°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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 991–1002, July, 2008. 相似文献
8.
A. E. Shchekotikhin D. A. Silaev E. P. Baberkina I. G. Makarov V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2002,38(5):543-546
The previously unknown 4,11-dimethoxynaphtho[2,3-f]indazole-5,10-dione has been obtained by the thermal cyclization of N-nitroso derivative of 2-acetamido-3-methyl-1,4-dimethoxyanthraquinone. 相似文献
9.
10.
V. Bobošík A. Krutošíková U. Jordis 《Monatshefte für Chemie / Chemical Monthly》1995,126(6-7):747-752
Summary A number of substituted 2,3-dimethylfuro[3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide2, which in turn was cyclized to give 2,3-dimethyl-5H-furo[3,2-c]pyridine-4-one (3) by heating at 240°C in Dowtherm. The pyridone3 was chlorinated with phosphorus oxychloride to give4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro[3,2-c]pyridine (5). Treatment of4 with several secondary heterocyclic amines led to compounds6a–6c. Reaction of pyridone3 with phosphorus pentasulfide rendered the thione7, which was methylated to8a. The 4-methoxy derivative8b was obtained from4 with sodium methoxide. 2,3,5-Trimethylfuro[3,2-c]pyridine-4-one (9) was obtained by reaction of3 with methyl iodide.Dedicated to Professor Dr.Fritz Sauter on the occasion of his 65th birthday 相似文献
11.
12.
N. Z. Tugusheva S. Yu. Ryabova N. P. Solov'eva V. G. Granik 《Chemistry of Heterocyclic Compounds》2002,38(12):1511-1517
A new method has been developed for the synthesis of derivatives of indolo[3,2-b]quinolines-11 based on N-oxidization of 2-nitro-10-substituted indolo[3,2-b]quinolines with subsequent conversion of the mixtures obtained into 2-nitro-11-substituted indolo[3,2-b]quinolinones-11. A series of 2-nitro-11-substituted indolo[3,2-b]quinolines was prepared. 相似文献
13.
A. E. Shchekotikhin E. P. Baberkina K. F. Turchin V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2001,37(8):944-948
4,11-Dihydroxynaphtho[2,3-f]indole-5,10-dione (pyrroloquinizarin), its 11-dehydroxy derivative, and Mannich base were synthesized by demethylation of previously obtained methoxynaphtho[2,3-f]indole-5,10-diones. 相似文献
14.
A. E. Shchekotikhin Y. N. Luzikov Y. B. Sinkevich V. N. Buyanov M. N. Preobrazhenskaya 《Chemistry of Heterocyclic Compounds》2008,44(10):1245-1249
On chlorination of 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione with sulfuryl chloride in chloroform, its mono-, di-, and trichloro derivatives are formed depending on
the conditions. Hydrolysis of the di- and trichloro derivatives gives a new polycondensed derivative of isatin, 4,11-dimethoxynaphtho-[2,3-f]isatin-5,10-dione. Its demethylation occurs effectively on extended heating with HBr in acetic acid and leads to 4,11-dihydroxynaphtho[2,3-f]isatin-5,10-dione (4,11-di-hydroxynaphtho[2,3-f]indole-2,3,5,10-tetraone).
*For Communication 6 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1532–1536, October, 2008. 相似文献
15.
16.
Yvonne Syha Charlene Valmalle Jan W. Bats Michael Kock Mona Abdel-Tawab Manfred Schubert-Zsilavecz 《Monatshefte für Chemie / Chemical Monthly》2006,137(10):1357-1364
Summary. Although various thiazoles are known in literature for their biological and pharmacological properties only a few multi-step
synthesis pathways for the preparation of thiazolo[3,2-a]pyrimidinones have been reported, which are tedious and time-consuming. An alternative synthesis pathway is described, which
allows the preparation of 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones in a one-step process based on a Michael-type tandem reaction. By heating of 2-thiobarbituric acid with ethyl 4-bromocrotonate in ethanol at 60°C for 2 h, a 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one was obtained in 73% yield, whereas carrying out the reaction at room temperature results in the formation
of an unstable unsaturated ester. The structures of both, the α,β-unsaturated ester as well as the 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one were confirmed by NMR spectroscopy. Additionally, the structure of the 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one was investigated by single-crystal X-ray analysis. The described approach offers a significant improvement
over previously reported synthesis pathways because it allows the simple preparation of 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones with good yields in a one-step reaction. 相似文献
17.
We have established that when 5-chloro-6-[cyano(2,3-dihydro-1-R-benzo[d]azol-2-yl)methyl]-2,3-pyrazinedicarbonitriles are reacted with nucleophilic reagents (aliphatic and aromatic amines, hydrogen sulfide), annelation of the five-membered ring occurs on the [b] face of the pyrazine with formation of 6-amino-7-hetaryl-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles and 6-amino-7-(1H-benzo[d]imidazol-2-yl)thieno[2,3-b]pyrazine-2,3-dicarbonitrile respectively. Further heating with excess of acylating reagent leads to formation of a novel heterocyclic system 1H-benzo[4,5]imidazo[1,2-c]pyrazino[2',3':4,5]pyrrolo[3,2-e]pyrimidine. Reaction of vicinal dinitriles with hydrazine hydrate leads to the novel system 1H-pyrrolo[2',3':5,6]pyrazino[2,3-d]pyridazine. 相似文献
18.
V. N. Britsun A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(3):396-402
We have studied the reaction of 2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-one and 2-aryl-2,3-dihydro-4H-[1,3]thiazino[3,2-a]benzimidazol-4-ones
with amines, alkylating reagents, and hydrogen peroxide. We have shown that the presence of an aryl substituent at the 2 position
of [1,3-thiazino[3,2-a]benzimidazol-4-ones has a substantial effect on the direction of the reactions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 445–452, March, 2006. 相似文献
19.
A. E. Shchekotikhin E. P. Baberkina K. F. Turchin V. N. Buyanov N. N. Suvorov 《Chemistry of Heterocyclic Compounds》2000,36(11):1284-1288
N-Acetylation and several N-alkylation reactions have been carried out for the previously synthesized 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione. 相似文献
20.
Natalia K. Utkina Aleksandra E. Makarchenko Pavel S. Dmitrenok 《Tetrahedron letters》2004,45(40):7491-7494
A new dipyrroloquinone, zyzzyanone A 1, having a pyrrolo[3,2-f]indole-4,8(1H,7H)-dione skeleton, was isolated from the Australian marine sponge Zyzzya fuliginosa, along with the known pyrroloquinoline alkaloids, makaluvamines C, E, G, H, and L, and damirones A and B. The structure of 1 was determined by spectroscopic data. Zyzzyanone A 1 shows moderate cytotoxic activity against mouse Ehrlich carcinoma cells (IC50 25 μg/mL), inhibits the cell division of fertilized sea urchin eggs at a concentration of 25 μg/mL, and exhibits UV-A and UV-B absorbing activity. 相似文献