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1.
Diaminomethylene- and aminomethylthiomethylenehydrazones [2] of cyclic ketones 1–8 readily reacted with ethoxymethylenemalononitrile to give spiro[cycloalkane-1,2′-[1,2′,4′]triazolo[1,5′-c]pyrimidine-8′-carbonitrile] derivatives 12–19 through the electrocyclic reaction of the initially formed condensation products 26 in moderate to high yields. The spiro[cyclopentanetriazolopyrimidine] derivatives underwent ring-opening at the cycloalkane moiety upon heating in solution to give 2-alkyl-5-substituted-[1,2,4]triazolo[1,5-c]pyrimidine-8′-carbonitriles 20–23 . When an alkyl substituent was introduced into the cyclopentane ring, cleavage of the spiro compounds occurred preferentially at the cyclopentane moiety between the spiro carbon and the more branched one. In contrast, the cyclohexane ring, especially of spiro-5-amino-triazolopyrimidines 17 and 18 strongly resisted to ring-opening under similar conditions, but those of 5-methylthiotriazolopyrimidines 14 gave up to 17 percent of cleavage after prolonged heating in hot ethanol. 2-t-Butyl-5-methylthio-2,3-dihydro[1,2,4]triazolo[1,5-c]pyrimidine-8-carbonitrile 25 [R3 = C(CH3)3] was highly susceptible to the cleavage even at room temperature and produced the corresponding 2-unsubstituted triazolopyrimidine 24 with loss of the t-butyl group. 相似文献
2.
Gbor Berecz Jzsef Reiter Gyula Argay Alajos Klmn 《Journal of heterocyclic chemistry》2002,39(2):319-325
Dedicated to Dr. János Császár on the occasion of his 70th birthday Ring transformation of 2‐cyanoimido‐3‐methyl‐1,3‐oxazolidine ( 10 ) yielded 5‐amino‐3‐[N‐(2‐hydrox‐yethyl)‐N‐methyl]amino‐1H‐1,2,4‐triazole ( 6 ) that was ring closed with different β‐keto esters to 2‐[N‐(2‐hydroxyethyl)‐N‐methyl]amino‐1,2,4‐triazolo[1,5‐a]pyrimidinones ( 4 ). Cyclisation of derivatives 4 led to imidazo[2′,1′:3,4][1,2,4]triazolo[1,5‐a]pyrimidines ( 2 ) and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5‐a]pyrim‐idines ( 3 ) representing 10 novel ring systems. Besides spectroscopical evidence of structure of derivatives 2 and 3 X‐ray diffraction analysis of derivative 2b was also performed. 相似文献
3.
《Journal of heterocyclic chemistry》2018,55(6):1450-1478
Novel [1,2,4]triazole derivatives were synthesized via various synthetic pathways. Among which were different substituted [1,2,4]triazole analogues that were synthesized, in addition to various fused [1,2,4]triazolo[1,5‐a]pyrimidine derivatives, [1,2,4]triazolo[1,5‐a][1,3,5]triazines, and [1,2,4]triazolo[5,1‐c][1,2,4]triazines. Besides, benzo[h][1,2,4]triazolo[5,1‐b]quinazolines, [1,2,4]triazolo‐[5,1‐b]quinazoline, [1,2,4]triazolo[1,5‐a]quinazoline and [1,2,4]triazolo[5,1‐d][1,2,3,5]tetrazine derivatives were also synthesized. The newly synthesized compounds were evaluated for their in vitro anticancer activity against liver cancer HepG2 and breast cancer MCF7 cell lines compared with the reference drug doxorubicin. Compounds 4 , 7 , 15 , 17 , 28 , 34 , and 47 were found to exert promising anticancer activity against HepG2 cell line showing IC50 values ranging from 17.69 to 25.4 μM/L, while compounds 7 , 14a , 17 , 28 , and 34 showed significant activity against MCF7 cell line with IC50 values ranging from 17.69 to 27.09 μM/L. 相似文献
4.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(6):1805-1807
Novel pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5, 6 and 8 were synthesized, and these compounds were converted into novel spiro[benzoxazole-2′,4(1H,3′H)-pyrazolo[5,1-c][1,2,4]triazines] 7 and 9 by ring transformation. 相似文献
5.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(4):1259-1262
The reactions of the 3-substituted 4-amino-8-ethoxycarbonyl[5,1-c][1,2,4]triazines 1 and 2 with o-amino-phenol hydrochloride gave the pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5 and 8 . The alkylation of 5 with methyl iodide and isopropyl iodide afforded the 6-alkoxylpyrazolo[1′,5′:3,4][1,2,4]triazino-[5,6-b][1,5]benzoxazepines 6a and 6b , respectively. Refluxing of 5, 6a, 6b and 8 in hydrochloric acid/acetic acid resulted in ring transformation to produce the spiro[benzoxazole-2′(3′H),4(1H)pyrazolo[5,1-c][1,2,4]-triazines] 7a, 7b and 9 . The screening data of the above compounds was described. 相似文献
6.
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
7.
Nehal M. Elwan 《Journal of heterocyclic chemistry》2004,41(2):281-284
Reaction of 1‐amino‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (1) with dimethylformamide‐dimethylacetal (DMF‐DMA) gave 1 ‐[N,N‐(dimethylaminomethylene)amino]‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (2). Compounds (1) reacted with triethylorthoformate yielding 1‐[N‐(ethoxymethylene)amino]‐3‐arylpyrido[1,2‐a]benzimidazole‐2,4‐dicarbonitrile (3). 3‐Amino‐4‐imino‐5‐aryl‐6‐cyanopyrimido[5′,4′:5,6]pyrido[1,2‐α] benzimidazole (4) was synthesized via condensation of either (2) or (3) with hydrazine hydrate. Reactions of (4) with acetic anhydride, ethyl chloroformate or aryl isothiocyanate yielded the respective derivative of the new ring system namely 1,2,4‐triazolo[2″,3″:6′,1′]pyrimido[4′,5′:2,3]pyrido[1,2‐a]benzimidazole (5–7). 相似文献
8.
[1,3]Thiazolo[2′,3′:3,4][1,2,4]triazolo[1,5‐a]pyrimidines – A New Heterocyclic System Accessed via Bromocyclization 下载免费PDF全文
Maksym Fizer Mikhailo Slivka Eduard Rusanov Alexandr Turov Vasil Lendel 《Journal of heterocyclic chemistry》2015,52(3):949-952
A facile access to novel condensed system of [1,3]thiazolo[2′,3′:3,4][1,2,4]triazolo[1,5‐a]pyrimidine is presented. This protocol consists of bromine‐assisted direct electrophilic heterocyclization of 3‐N‐allylamine‐5,6‐dihydro[1,3]thiazolo[2,3‐c][1,2,4]triazole. The bromination took place in acetic acid and gave a good yield of the target product, which was dehydrobrominated by sodium acetate action. 相似文献
9.
T. Ramalingam M. S. R. Murty Y. V. D. Nageswar P. B. Sattur 《Journal of heterocyclic chemistry》1990,27(4):981-982
The reaction of 3 -amino-1,2,4-triazolo[4,3-a]quinoline ( II ) with diethyl ethoxymethylenemalonate and ethyl acetoacetate/ethyl trifluoroacetoacetate afforded 10-carboethoxy-9-oxo-9H-pyrimido[1′,2′:1,5][1,2,4]triazolo-[4,3-a]quinoline ( III ) and 11-methyl/trifluoromethyl-9-oxo-9H-pyrimido[1′,2′:1,5][1,2,4]triazolo[4,3-a]quinoline ( IV/V ) respectively. 2-Chloropyridine-3-carboxylic acid chloride reacted with II to yield 5-oxo-5H-pyrido-[3″,2″:5′,6′]pyrimido[1′,2′:1,5][1,2,4]triazolo[4,3-a]quinoline ( VII ), a new ring system. 相似文献
10.
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
11.
Yoshiko Miyamoto Chiji Yamazaki Megumi Matzui 《Journal of heterocyclic chemistry》1990,27(6):1553-1557
Treatment of certain diaminomethylenehydrazones 1 of aromatic carbonyl compounds with ethyl N-cyanoimidate ( 2 ) in acetonitrile in the presence of a tertiary amine at room temperature gives the corresponding amino(N-cyanoiminomethyl)aminomethylenehydrazones 3 in high yields. The intermediate 3 can readily be cyclized to the corresponding 5-amino-2,3-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines 4 in moderate to good yields by brief heating in acetonitrile. When the reaction of diaminomethylenehydrazones 1 with ethyl N-cyanoimidate ( 2 ) is performed at reflux temperature in the presence of a tertiary amine, 5-amino-2,3-dihydro[1,2,4]triazolo[1,5-a]1,3,5]triazines 4 can be directly obtained in moderate yields. The yields of triazolotriazine produced by the one-step synthesis are generally comparable or even higher than the overall yields from the two-step procedure. 相似文献
12.
Montserrat Heras David Font Anthony Linden JosM. Villalgordo 《Helvetica chimica acta》2003,86(9):3204-3214
The synthesis of novel triazolo[1,5‐a]triazin‐7‐ones is presented. Starting from 3‐amino‐5‐sulfanyl‐1,2,4‐triazole, the synthetic sequence involved alkylation with benzyl bromide, reaction with p‐nitrophenyl chloroformate followed by treatment with a primary amine, and condensation with diethoxymethyl acetate. Final oxidation of the thioether moiety with 3‐chloroperbenzoic acid provided 2‐(benzylsulfonyl)[1,2,4]triazolo[1,5‐a][1,3,5]triazin‐7‐ones 5a and 5b in good overall yields. Treatment of 5a and 5b with secondary amines provided highly functionalized [1,2,4]triazoles through an unexpected triazinone ring opening. A mechanism for this transformation is proposed. 相似文献
13.
4‐Hydrazino‐2‐methylpyrimidino[4′,5′:4,5]thiazolo[3,2‐a]benzimidazole ( 4 ) was obtained from hydrazinolysis of the 4‐chloro derivative 3 with hydrazine hydrate. The hydrazino derivative 4 was further cyclized to the corresponding pyrazole 5 , pyrazolone 6 and 5‐methyl‐1,2,4‐triazolo[1″,5″:3′,4′]pyrimidino[5′,6′:5,4]‐thiazolo[3,2‐a]benzimidazole ( 9 ) and 5‐methy‐1,2,4‐triazolo[4″,3″:3′,4′]pyrimidino[5′,6′:5,4]thiazolo‐[3,2‐a]benzimidazole ( 10 ), respectively. The triazolo derivative 10 was isomerized to the triazolo derivative 9 under a variety of reaction conditions. 相似文献
14.
Gbor Berecz Lszl Pong Istvn Kvesdi Jzsef Reiter 《Journal of heterocyclic chemistry》2002,39(2):327-334
Dedicated to Professor András Messmer on the occasion of his 80th birthday The reaction of differently substituted 5‐amino‐1,2,4‐triazoles ( 5 ) with isothiourea derivatives ( 3 ) to yield isomeric 5,7‐diamino‐1,2,4‐triazolo[1,5‐a][1,3,5]triazines ( 6 and 7 ), previously described as not proceeding in melt, was performed in different solvents as well as in the melt at 150‐160°. It was proved that the above reaction had rather general validity. The structure of isomers 6 and 7 were proved spectroscopically. The structure of 6/5 (Q = ethylamino) was corroborated with single crystal X‐ray diffraction determination, as well. 相似文献
15.
Victoria V. Lipson Nataliya V. Svetlichnaya Victoria V. Borodina Maria G. Shirobokova Sergey M. Desenko Vladimir I. Musatov Svetlana V. Shishkina Oleg V. Shishkin Roman I. Zubatyuk 《Journal of heterocyclic chemistry》2012,49(5):1019-1025
Formylation of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine 1a using Vilsmeier–Haack conditions yields 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylcarbaldehyde 3a . 5,7‐Diaryl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidines 1b , 1c in this reaction apart from formylation undergo recyclization into 5‐aryl‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylmethane derivatives 4b , 4c , 5b , 5c , and 6 . The structure of the synthesized compounds was determined on the basis of NMR, IR, and MS spectroscopic data and confirmed by the X‐ray analysis of the 6‐(ethoxy‐phenyl‐methyl)‐5‐phenyl‐[1,2,4]triazolo[1,5‐a]pyrimidine 6 , 5‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[1,5‐a]pyrimidine 11 , and 7‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[4,3‐a]pyrimidine 12 . 相似文献
16.
Reaction of 4-amino-2-methylbenzimidazo[1,2-a][1,3,5]triazines 2 with diethyl ethoxymethylenemalonate afforded 3-carboethoxy-6-methyl-4-oxo-4H-pyrimido[1′,2′:5,6][1,3,5]triazino[1,2-a]benzimidazoles 3 , a new ring system. 相似文献
17.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
18.
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
19.
Yoshihisa Kurasawa Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(6):1799-1801
Novel 3-substituted 4-amino-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazines 7,8 were synthesized by the reactions of malononitrile and ethyl cyanoacetate with the pyrazole-5-diazonium salt 3 . Moreover, compounds 7,8 were converted into the pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepines 9, 10 . 相似文献
20.
B. A. Demidchuk V. S. Brovarets A. N. Chernega J. A. K. Howard A. N. Vasilenko A. V. Turov B. S. Drach 《Russian Journal of General Chemistry》2007,77(3):474-481
Reactions of polychlorinated 2-aza-1,3-dienes of the general formuls ArCCl=NCCl=CCl2 with 3(5)-aminopyrazoles, 3(5)-amino-1,2,4-triazoles, and 5-aminotetrazole led to the formation of substituted pyrazolo[1,5-a][1,3,5]triazines, [1,2,4]triazolo[1,5-a][1,3,5]triazines, and 2-azido-1,3,5-triazine derivatives whose structure was reliably established by spectral methods and X-ray analysis. 相似文献