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1.
H. S. El‐Kashef A. M. Kamal El‐Dean A. A. Geies J. C. Lancelot P. Dallemagne S. Rault 《Journal of heterocyclic chemistry》2000,37(6):1521-1526
The synthesis of the title compounds was achieved using the key intermediate ethyl 4,6‐dimethyl‐3‐(pyrrol‐1‐yl)thieno[2,3‐b]pyridine‐2‐ carboxylate 2. This latter compound was obtained via the interaction of the thienopyridine amino ester 1 with 2,5 dimethoxytetrahydrofuran in acidic medium. 相似文献
2.
Essam Kh. Ahmed 《Heteroatom Chemistry》2002,13(3):280-286
Diethyl 2‐[(ethoxythioxomethyl)amino]‐4,5,6,7‐tetrahydrothieno[2,3‐c]‐pyridine‐3,6‐dicarboxylate 2 , prepared from diethyl 2‐isothiocyanato‐4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine‐3,6‐dicarboxylate 1 by boiling in anhydrous ethanol, was converted into pyrido[4′,3′:4,5]thieno[2,3‐d]pyrimidine derivatives 3, 4 by treatment with hydrazine hydrate. The tetracyclic systems imidazo[1,2‐a]pyrido‐[4′,3′:4,5]thieno[2,3‐d]pyrimidine 9 and pyrido[4′,3′:4,5]thieno[2,3‐d][1,3]thiazolo‐[3,2‐a]pyrimidine 10 were synthesized by the reaction of 2 with 1,2‐diaminoethane and aminoethanethiol, respectively. The hydrazino derivative 4 underwent cyclization reactions with orthoesters and nitrous acid to give the corresponding pyrido[4′,3′:4,5]thieno[2,3‐d][1,2,4]triazolo[1,5‐a]pyrimidines 5, 6 and pyrido[4′,3′:4,5]thieno[3,2‐e][1,2,3,4]tetrazolo[1,5‐a]pyrimidine 8 , respectively. Moreover, reactions of 3 with cyanogen bromide, N‐carbethoxyhydrazine, carbon disulfide, and ethylchloroformate resulted in the formation of the new pyrido[4′,3′:4,5]thieno[2,3‐d][1,3,4]thiadiazolo[3,2‐a]pyrimidine derivatives 12–15 . © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:280–286, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10030 相似文献
3.
The cyclocondensation of 5‐hydroxy‐pyrido[2,3‐d]pyrimidines 1 with malonates gives pyrano[2′,3′:4,5]‐pyrido[2,3‐d]pyrimidines 2 . Nitration of 1 and reduction with zinc in the presence of carboxylic acids/anhydrides gave 2‐alkyloxazolo[5′,4′:4,5]pyrido[2,3‐d]pyrimidines 4 , which were ring‐opened to 6‐aminopyrido[2,3‐d]pyrimidines 5, 6 and 7 . Cyclization of 6‐aminopyrido[2,3‐d]pyrimidines 6 with benzoylchlorides 8 gave 2‐aryloxazolo[5′,4′:4,5]pyrido[2,3‐d]pyrimidines 9 . Reaction conditions for the cyclization have been studied by differential scanning calorimetry (DSC). 相似文献
4.
2,3‐Dihydro‐1,3,4‐thiadiazoles, pyrazoles, pyrazolo[3,4‐d]pyridazines, thieno[2,3‐b]pyridines, pyrim‐idino[4′,5′:4,5]thieno[2,3‐b]pyridines and pyrrolo[3,4‐d]pyrazoles were obtained in a good yields by treatment of hydrazonoyl halides with each of alkyl carbodithioates, 3‐(dimethylamino)‐1‐naphtho[1,2‐d]furan‐2‐ylprop‐2‐en‐1‐one and N‐arylmalemides. 相似文献
5.
Karl Schnafinger Christine M. Yasenchak Anne Vollman Helen H. Ong 《Journal of heterocyclic chemistry》1988,25(2):535-537
A series of structurally novel 7,8,9,10-tetrahydropyrido[3′,4′:4,5]pyrrolo[2,3-c,]quinolines, 4a-c , were synthesized via a facile Fischer indole cyclization from the appropriately substituted hydrazinoquinolines 2a-c . Acetamides 4a,c were hydrolyzed to 5a,b and further converted to tertiary amines 6a-c . Potent antihypertensive activity has been observed with a number of the title compounds as well as the intermediate 3a . 相似文献
6.
7.
One‐pot Sequential Reactions Featuring a Copper‐catalyzed Amination Leading to Pyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines and Dihydropyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines 下载免费PDF全文
Tetracyclic skeletons combining an imidazo[1,2‐a]pyridine moiety with a quinoline framework such as pyrido[2′,1′:2,3]imidazo[4,5‐b]quinoline are stimulating increasing interests since they are close isosteres of a series of powerful antiproliferative compounds. In this paper, we report a novel methodology for the synthesis of pyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines through one‐pot sequential reactions of commercially available or readily obtainable 2‐aminopyridines, 2‐bromophenacyl bromides, aqueous ammonia, and aldehydes. Moreover, dihydropyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines could also be obtained in a similar manner by using various ketones as the substrates in place of aldehydes. Notably, the whole procedure combines condensation/amination/cyclization reactions in one pot to give complex compounds in a simple and practical manner. Compared with literature methods, the synthetic strategy reported herein has the advantages of readily available starting materials, structural diversity of products, good functional group tolerance, and obviation of step‐by‐step operations. 相似文献
8.
Syntheses of substituted pyrazolo[3,4-b]quinolines, 3,4-dihydro-4-oxopyriraido[4′,5′:4,5]theino[2,3-b]quinoline and 12-phenylpyrido[1′,2′:1,2[pyrimido[4,5-b]quinoline are described. 相似文献
9.
Toshinobu Suzuki Yasushi Nagae Keiryo Mitsuhashi 《Journal of heterocyclic chemistry》1986,23(5):1419-1421
Novel synthesis of the title compounds by the facile cyclization between 2,3-dichloro-5,6-dicyanopyrazine and various 2-aminopyridines under relatively mild conditions is described. The reactivity depended on the basicity of 2-aminopyridines. 相似文献
10.
2‐Acyl‐3‐aminonaphtho[2,1‐b]furan ( 1 ) reacts with activated methylene such as malono nitrile or ethyl cyanoacetate to afford naphtho[1′,2′:4,5]furo[3,2‐b]pyridine 2a,b . Chloroacylation of the amino group in compound ( 1 ) gave compound 3 which reacts with different amines to produce compound 4 . 相似文献
11.
Aileen Pfleider Halverson Lyle W. Castle Raymond N. Castle 《Journal of heterocyclic chemistry》1996,33(1):179-183
Naphtho[1′,2′:4,5]thieno[2,3-c][1,10]phenanthroline and naphtho[2′,1′:4,5]thieno[2,3-c][1,10]phenanthroline, two novel polycyclic heterocyclic ring systems, have been synthesized in four steps from known starting materials. The total 1H nmr spectral assignments were made using a COSY experiment to identify the spin systems. 相似文献
12.
Victor M. Chernyshev Dmitry A. Khoroshkin Andrey N. Sokolov Vitaly A. Taranushich Eugene S. Gladkov Svetlana V. Shishkina Oleg V. Shishkin Sergey M. Desenko 《Journal of heterocyclic chemistry》2008,45(5):1419-1427
2′‐Substituted 5′,6′,7′,8′‐tetrahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 3a‐d were synthesized by condensation of 3‐substituted 5‐amino‐1,2,4‐triazoles 1a‐d with 2‐cyclohexylidene cyclohexanone 2 in DMF. The compounds 3 were hydrogenated with sodium borohydride in ethanol to give 2′‐substituted cis‐4a',5′,6′,7′,8′,8a'‐hexahydro‐4′H‐spiro[cyclohexane‐1,9′‐[1,2,4]triazolo[5,1‐b]quinazolines] 4a‐d in high yields. The reactions of alkylation, acylation and sulfonylation of the compounds 4 were studied. The structure of the synthesized compounds was determined on the basis of NMR measurements including HSQC, HMBC, NOESY techniques and confirmed by the X‐ray analysis of 6 and 11b . The described synthetic protocols provide rapid access to novel and diversely substituted hydrogenated [1,2,4]triazolo[5,1‐b]quinazolines. 相似文献
13.
John P. Paolini Frank P. Palopoli Louis J. Lendvay John Huffman 《Journal of heterocyclic chemistry》1987,24(3):549-553
The reaction of 2-aminopyridine, o-phthaldehydic acid and potassium cyanide gave pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one, which upon treatment with propargylbromide, yielded both O and N alkylated products. 2-Aminopyridine, o-phthaldehyde and potassium cyanide gave 1-cyano-2-(2-pyridyl)isoindole which rearranged in acid to give the previously unreported parent pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinole. Structures were confirmed using uv, ir, nmr and x-ray spectroscopy. 相似文献
14.
William B. Wright George O. Morton Andrew S. Tomcufcik 《Journal of heterocyclic chemistry》1979,16(7):1345-1347
Reactions of 2,3-dichloroquinoxalines with 2-(hydroxymethyl)piperidine resulted in a series of 1,2,3,4,4a,5-hexahydropyrido[1′,2′:4,5][1,4]oxazino[2,3-b]quinoxaline derivatives. The structures of the products were confirmed by nmr and x-ray crystallography. 相似文献
15.
16.
Gerardo Blanco Jos M. Quintela Carlos Peinador 《Journal of heterocyclic chemistry》2006,43(4):1051-1056
An efficient one‐pot access for the synthesis of the previously unreported tetracyclic fused pyrimido‐[4″,5″:4′,5′]thieno[3′,2′:4,5]thieno[3,2‐d]pyrimidine ( 3 ) and 1,2,3‐triazine[4″,5″:4′,5′]thieno‐[3′,2′:4,5]thieno‐[3,2‐d]‐1,2,3‐triazine ( 5 ) heteroaromatic nitrogen ligands is described. The title compounds 3 and 5 were obtained from 3,4‐diaminothieno[2,3‐b]thiophene‐2,5‐dicarbonitrile and phosgeniminium chloride and sodium nitrite/HCl, respectively. Substituted condensed thieno[2,3‐b]thiophene derivatives 4 and 6 were synthesized by nucleophilic displacement of the chloroderivatives 3 and 5 . 相似文献
17.
A series of monomethoxynaphtho[1′,2′:4,5]thieno[2,3-c]quinolines has been prepared by photocyclization of the appropriate N-methoxyphenyl-1-chloronaphtho[2,1-b]thiophene-2-carboxamides. Some of the lactams obtained were converted into the thiolactams and their S-methyl derivatives. The lactams were also converted into the corresponding 6-chloro derivatives. Some of these were catalytically dechlorinated into the monomethoxynaphtho[1′,2′:4,5]thieno[2,3-c]quinolines which were then quaternized into the N-methyl quaternary salts. 相似文献
18.
Joseph P. Yevich John R. Murphy Richard F. Dufresne Philip L. Southwick 《Journal of heterocyclic chemistry》1978,15(8):1463-1470
Compounds in the new pyrrolo[3′,4′:4,5]pyrrolo[3,4-b]indole series have been produced by an imide cyclization of appropriate derivatives of pyrrolo[3,4-b]indole. 相似文献
19.
Fabrizio Melani Lucia Cecchi Vittoria Colotta Giovanna Palazzino Guido Filacchioni 《Journal of heterocyclic chemistry》1988,25(5):1367-1371
By reacting 2-chloronicotinoyl chloride with acetyl or benzoyl acetate, ethyl 2-methyl- or 2-phenyl-4-oxopyrano[2,3-b]pyridine-3-carboxylates were prepared. The nucleophilic rearrangement of the latter with hydrazines gave rise to the title compounds. 相似文献
20.
Maisa I. Abdel Moneam Ahmed A. Geies Galal M. El‐Naggar Soliman M. Mousa 《中国化学会会志》2004,51(6):1357-1366
Sodium salt of 4‐hydroxy‐6‐methyl‐2‐phenylpyrimidine‐5‐carbonitrile ( 3 ) was subjected to alkylation with different a‐halo compounds, where the corresponding O‐alkylated products 4a‐g were obtained. Ring closure of the O‐alkylated product 4a‐c performed using sodium ethoxide in refluxing ethanol afforded furo[2,3‐d]pyrimidines 5a‐c The latter compounds on reaction with a variety of reagents gave other new furopyrimidines as well as a number of furodipyrimidines. 相似文献