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1.
Microwave‐assisted Synthesis of 6‐{(5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines
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Sreenivas Avula Jayaram Reddy Komsani Satish Koppireddi Rambabu Yadla 《Journal of heterocyclic chemistry》2015,52(6):1737-1742
An efficient and convenient synthesis of a new series of 2‐{(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)methyl}‐5‐aryl‐1,3,4‐oxadiazoles from readily available 1,2‐diaminobenzene and isatins under microwave irradiation conditions was disclosed. The 6‐{(5‐aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines were also prepared by the thermal cyclo‐condensation reaction of 2‐(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)acetohydrazides with carboxylic acids in refluxing POCl3. The microwave‐assisted synthesis was rapid and resulted in higher yield of the products at lower operating temperature with reduced waste generation in comparison with the thermal reaction protocol. 相似文献
2.
Ho Sik Kim Sam Tag Kwag Kyung Ok Choi Yoshihisa Okamoto Shinnosuke Kajiwara Noriko Fujiwara Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》2000,37(1):103-107
The reaction of 6‐chloro‐2‐hydrazinoquinoxaline 4‐oxide 1b with acetylacetone or benzoylacetone gave 6‐chloro‐2‐(3,5‐dimethylpyrazol‐i‐yl)quinoxaline 4‐oxide 5a or 6‐chloro‐2‐(3‐methyl‐5‐phenylpyrazol‐1‐yl)quinoxaline 4‐oxide 5b , respXectively. Compound 5a or 5b was converted into the pyrrolo[1,5‐a]quinoxaline 6a or 6b , triazolo[4,3‐a]quinoxaline 9a or 9b , and tetrazolo[1,5‐a]quinoxaline 10. 相似文献
3.
[1,2,5]thiadiazolo[3,4‐g]quinoxaline acceptor‐based donor–acceptor–donor‐type polymers: Effect of strength and size of donors on the band gap
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Gurcan Gokce Baris Karabay Atilla Cihaner Merve Icli Ozkut 《Journal of polymer science. Part A, Polymer chemistry》2017,55(20):3483-3493
Electrochromic polymers based on [1,2,5]thiadiazolo[3,4‐g]quinoxaline acceptor and thiophene, 3,4‐ethylenedioxythiophene and 3,3‐didecyl‐3,4‐proylenedioxythiophene donors, namely poly(6,7‐diphenyl‐4,9‐di(thiophen‐2‐yl)‐[1,2,5]thiadiazolo[3,4‐g]quinoxaline) ( P1 ), poly(4‐(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐9‐(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐7‐yl)‐6,7‐diphenyl‐[1,2,5]thiadiazolo[3,4‐g]quinoxaline) ( P2 ), and poly(4‐(3,3‐didecyl‐3,4‐dihydro‐2H‐thieno[3,4‐b][1,4]dioxepin‐6‐yl)‐9‐(3,3‐didecyl‐3,4‐dihydro‐2H‐thieno[3,4‐b][1,4]dioxepin‐8‐yl)‐6,7‐diphenyl‐[1,2,5]thiadiazolo[3,4‐g]quinoxaline) ( P3 ), respectively, were electrochemically and/or chemically synthesized and characterized. Electrochemical and optical properties of the polymers were then investigated. The results, which were obtained electrochemically and optically, indicate that the polymers bearing the same acceptor and different donor units have a band gap range of 0.59–1.24 eV depending on the strength and size of the donor units and band gap determination method. A significant finding in this study was the phenomenon that when the acceptor is physically huge, the general rule that a weak donor would have a high band gap whereas a strong donor would have low band gap can be broken due to the torsional angles/steric hindrances involved with physically large donor molecules. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 3483–3493 相似文献
4.
Syntheses of New Unsymmetrical 2,5‐Disubstituted‐1,3,4‐oxadiazoles and 1,2,4‐Triazolo[3,4‐b]‐1,3,4‐thiadiazoles Bearing Thieno[2,3‐c]pyrazolo Moiety
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Shivaraj P. Patil Shrikant B. Kanawade Dinesh C. Bhavsar Prashant S. Nikam Sachin A. Gangurde Raghunath B. Toche 《Journal of heterocyclic chemistry》2014,51(2):368-373
New series of (thieno[2,3‐c]pyrazolo‐5‐yl)‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazoles 10a , 10b , 10c and (thieno[2,3‐c]pyrazol‐5‐yl)‐1,3,4‐oxadiazol‐3(2H)‐yl)ethanones 6a , 6b , 6c has been synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide 3 by multistep reaction sequence. (5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)‐1H‐thieno[2,3‐c]pyrazoles 4a , 4b , 4c were also synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide 3 by cyclization with various aromatic carboxylic acids. The hydrazide 3 was obtained by reaction of thieno[2,3‐c]pyrazole‐5‐carboxylate 2 with hydrazine hydrate in good yield, and compound 2 was obtained by the reaction of 5‐chloro‐3‐methyl‐1‐phenyl‐1H‐pyrazole‐4‐carbaldehyde 1 and 2‐ethyl thioglycolate in presence of sodium alcoholate in good yield. 相似文献
5.
Yoshihisa Kurasawa Kazunori Sakurai Shinnosuke Kajiwara Kazuho Harada Yoshihisa Okamoto Ho Sik Kim 《Journal of heterocyclic chemistry》2000,37(5):1257-1263
The reaction of the 2‐(1‐alkylhydrazino)‐6‐chloroquinoxaline 4‐oxides 1a,b with diethyl acetone‐dicarboxylate or 1,3‐cyclohexanedione gave ethyl 1‐alkyl‐7‐chloro‐3‐ethoxycarbonylmethylene‐1,5‐dihydropyridazino[3,4‐b]quinoxaline‐3‐carboxylates 5a,b or 6‐alkyl‐10‐chloro‐1‐oxo‐1,2,3,4,6,12‐hexahydroquinoxalino[2,3‐c]cinnolines 7a,b , respectively. Oxidation of compounds 5a,b with nitrous acid afforded the ethyl 1‐alkyl‐7‐chloro‐3‐ethoxycarbonylmethylene‐4‐hydroxy‐1,4‐dihydropyridazino‐[3,4‐b]quinoxaline‐4‐carboxylates 9a,b , whose reaction with base provided the ethyl 2‐(1‐alkyl‐7‐chloro‐4‐oxo‐1,4‐dihydropyridazino[3,4‐b]quinoxalin‐3‐yl)acetates 6a,b , respectively. On the other hand, oxidation of compounds 7a,b with N‐bromosuccinimide/water furnished the 4‐(1‐alkyl‐7‐chloro‐4‐oxo‐1,4‐dihydropyridazino[3,4‐b]quinoxalin‐3‐yl)butyric acids 8a,b , respectively. The reaction of compound 8a with hydroxylamine gave 4‐(7‐chloro‐4‐hydroxyimino‐1‐methyl‐1,4‐dihydropyridazino[3,4‐b]quinoxalin‐3‐yl)‐butyric acid 12 . 相似文献
6.
Padmakar A. Suryavanshi Dr. Vellaisamy Sridharan Prof. J. Carlos Menéndez 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(39):13207-13215
The cerium(IV) ammonium nitrate (CAN)‐catalyzed sequential multicomponent reaction between tryptamine, α,β‐unsaturated aldehydes, and β‐dicarbonyl compounds affords highly substituted indolo[2,3‐a]quinolizines in a single synthetic operation. Two rings are generated through the creation of two C? C and two C? N bonds by a domino process comprising initial β‐enaminone formation, followed by individual Michael addition, 6‐exo‐trig cyclization, iminium formation, and Pictet–Spengler steps. Furthermore, the reaction is diastereoselective and affords exclusively compounds with a trans relationship between the H‐2 and H‐12b protons. The use of amines bearing a less nucleophilic side chain aromatic ring (5‐bromotryptamine, 3,4‐dimethoxyphenylethylamine) prevents the Pictet–Spengler final step and leads to N‐indolylethyl or N‐phenylethyl‐1,4‐dihydropyridines, which are cyclized to the corresponding indolo[2,3‐a]quinolizines or benzo[a]quinolizines in the presence of HCl in methanol/water. Treatment of the fused quinolizine derivatives with sodium triacetoxyborohydride led to the corresponding indolo[2,3‐a]quinolizidines or benzo[a]quinolizidines, possessing four stereogenic centers, as mixtures of two diastereomers. 相似文献
7.
The reaction of 3‐(benzothiazol‐2‐yl)‐3‐oxopropanenitrile 1 with active methylene reagents 2a–d and sulfur afforded polysubstituted thiophenes 3a–c . The synthetic potential of the β‐enaminonitrile moiety in 3a was explored. The reaction of 3a with active methylene reagents 2a–e afforded thieno[2,3‐b]pyridine derivatives 6–8. Refluxing of 3a with acetic anhydride alone, with acetic anhydride/pyridine mixture, or with carbon disulfide in pyridine afforded the acetamido 9, thieno[2,3‐d]pyrimidine 10, and pyrimidinedithiol 11 derivatives, respectively. The pyrimidinedithiol 11 was alkylated smoothly with methyl iodide to give the bis(methylthio) derivative 12. Also, compound 3a reacted with trichloroacetonitrile to give the thieno[2,3‐d]pyrimidine derivative 14. Compound 3a reacted with triethyl orthoformate or formamide to give the ethoxymethylideneamino 15 and thieno[2,3‐d]pyridine 16, respectively. Compound 15 reacted with hydrazine to afford thieno[2,3‐d]pyridine 17, which reacted with various reagents such as chloroacetyl chloride, ethyl cyanoacetate, diethyl oxalate, or chloroethylformate to give 1,2,4‐triazolo[1,5:1,6]pyrimidino‐[4,5‐b]thiophene derivatives 18a–c and 19, respectively. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:94–101, 2000 相似文献
8.
Ho Sik Kim Geuk Jeong Hyoung Choul Lee Jin Hee Kim Yong Tae Park Yoshihisa Okamoto Shinnosuke Kajiwara Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》2000,37(5):1277-1280
The reaction of the quinoxaline N‐oxide 1 with thiophene‐2‐carbaldehyde gave 6‐chloro‐2‐[1‐methyl‐2‐(2‐thienylmethylene)hydrazino]quinoxaline 4‐oxide 5 , whose reaction with 2‐chloroacrylonitrile afforded 8‐chloro‐2,3‐dihydro‐4‐hydroxy‐1‐methyl‐3‐(2‐thienyl)‐1H‐1,2‐diazepino[3,4‐b]quinoxaline‐5‐carbonitrile 6 . The reaction of compound 6 with various alcohols in the presence of a base effected alcoholysis to provide the 5‐alkoxy‐8‐chloro‐2,3,4,6‐tetrahydro‐1‐methyl‐4‐oxo‐3‐(2‐thienyl)‐1H‐1,2‐diazepino[3,4‐b]‐quinoxalines 7a‐d . The reaction of compounds 7a and 7b with diethyl azodicarboxylate effected dehydrogenation to give the 5‐alkoxy‐8‐chloro‐4,6‐dihydro‐1‐methyl‐4‐oxo‐3‐(2‐thienyl)‐1H‐1,2‐diazepino[3,4‐b]‐quinoxalines 8a and 8b , respectively. Compounds 8a and 8b were found to show good algicidal activities against Selenastrum capricornutum and Nitzchia closterium. 相似文献
9.
Yoshihisa Kurasawa Waka Satoh Izumi Matsuzaki Yuka Maesaki Yoshihisa Okamoto Ho Sik Kim 《Journal of heterocyclic chemistry》2003,40(5):837-843
The reaction of the quinoxaline N‐oxides 7a,b with diethyl ethoxymethylenemalonate gave the 1‐methylpyridazino[3,4‐b]quinoxaline‐4,4‐dicarboxylates 8a,b , whose reaction with N‐bromosuccinimide or N‐chlorosuccinimide afforded the 3‐halogeno‐1‐methylpyridazino[3,4‐b]quinoxaline‐4,4‐dicarboxylates 9a‐d. The reaction of compounds 9a‐d with hydrazine hydrate resulted in hydrolysis and decarboxylation to provide the 3‐halogeno‐1‐methylpyridazino[3,4‐b]quinoxaline‐4‐carboxylates 10a‐d , whose reaction with nitrous acid effected oxidation to furnish the 3‐halogeno‐4‐hydroxy‐1‐methylpyridazino[3,4‐b]quinoxaline‐4‐carboxylates 11a‐d , respectively. The reaction of compounds 11a‐d with hydrazine hydrate afforded the 3‐halogeno‐1‐methylpyridazino[3,4‐b]quinoxalin‐4‐ols 12a‐d , whose oxidation provided the 3‐halogeno‐1‐methylpyridazino[3,4‐b]quinoxalin‐4(1H)‐ones 6a‐d , respectively. Compounds 6a‐d had antifungal activities in vitro. 相似文献
10.
In the article the study of cyclocondensation of 3‐[2‐amino‐3‐(3,5‐dioxo‐2,3,4,5‐tetrahydro[1,2,4]‐triazme‐6‐yl)phenyl]‐2,3‐dihydro‐quinoxalin‐2‐one 5 is described and it was found, that the reaction does not proceed by both possible directions, but only cyclization with the carbonyl group of 6‐azauracile cycle proceeds. The 6‐(3‐oxo‐3,4‐dihydro‐quinoxaline‐2‐yl)‐4H‐2,3‐dihydro[1,2,4]triazino[5,6‐b]indol‐3‐one 6 was formed in this way. This course of cyclocondensation was confirmed by the fact, that the product 6 , mentioned above, is quite different from isomeric compound 7 , prepared unambiguously by condensation of 7‐(6‐azauracile‐5‐yl)isatine 8 with o‐phenylenediamine. 相似文献
11.
Yoshihisa Kurasawa Ayaka Kawase Jun Takizawa Yuka Maesaki Eisuke Kaji Yoshihisa Okamoto Ho Sik Kim 《Journal of heterocyclic chemistry》2005,42(4):551-556
The 3‐amino‐1‐methylpyridazino[3,4‐b]quinoxalin‐4(1H)‐one 6 and N‐(1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxalin‐3‐yl)carbamates 17a,b were synthesized from the 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxa‐line‐3‐carboxylate 1b via the 1,5‐dihydro‐4‐hydroxy‐1‐methylpyridazino[3,4‐b]quinoxaline‐3‐carbohydrazide 13b and then 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxaline‐3‐carboxazide 8 . Heating of compound 13b and arylalde‐hydes afforded the 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxaline‐3‐carbo(2‐arylmethylene)hydrazides 14a‐d. 相似文献
12.
《Journal of heterocyclic chemistry》2017,54(5):2874-2880
In the present investigation, the synthesis of a series of structurally new and interesting tert‐butyl‐ and bromo‐functionalized [1,2,4]triazino[5,6‐b ]indoles ( 6a – f ) and indolo[2,3‐b ]quinoxalines ( 8a – f ) has been achieved, involving the condensation reaction of 7‐bromo‐5‐tert‐butylisatins ( 4a – f ) with thiosemicarbazide ( 5 ) and benzene‐1,2‐diamine ( 7 ). The substrates 4a – f were prepared through bromination reaction of 5‐tert‐butylisatin ( 3 ) with NBS in PEG‐400 followed by alkylation reaction. The molecular structures of these newly synthesized compounds were elucidated on the basis of their elemental analyses and spectral data. 相似文献
13.
The synthesis of a new series of 5‐oxy‐pyrido[2,3‐b]quinoxaline‐9‐carboxamides 4a‐i and N1,N2‐Bis(5‐oxy‐pyrido[2,3‐b]quinoxaline‐9‐benzoyl)ethylenediamine ( 5 ) is reported starting from 2‐chloro‐3‐nitropyri‐dine. Fundamental steps of the synthetic pathway are i) preparation of 2‐(3‐nitro‐pyridin‐2‐ylamino)benzoic acid ( 1 ) via copper‐catalyzed condensation of 2‐chloro‐3‐nitropyridine with o‐anthranilic acid, ii) intramolecular cyclization of the acid 1 to 5‐oxy‐pyrido[2,3‐b]quinoxaline‐9‐carboxylic acid ( 2b ) upon treatment with concentrated sulfuric acid and oleum and iii) conversion of the acid 2 to the desired amides 4a‐i and 5 . Compounds 4a‐i and 5 are oxygenated azaanalogs of phenazines, a wellknown series of intercalators with cytotoxic activity. 相似文献
14.
Mohamed A. M. Gad‐Elkareem Mohamed A. A. Elneairy Adel M. Taha 《Heteroatom Chemistry》2007,18(4):405-413
6‐Aminopyridine‐2(1H)thiones 1 reacting with α‐halo‐compounds 2a–c afforded the alkylthiopyridine derivatives 3a–c which in turn cyclized to the corresponding thieno[2,3‐b]pyridine derivatives 4a–c . Several thieno[2,3‐b]pyridine derivatives 7, 16, 19 , pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine derivatives 6a,b, 11a–c, 21 and pyrido[3′,2′:4,5]thieno[3,2‐c]pyridazine derivatives 13, 17 were prepared starting from compounds 4a–c . © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:405–413, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20313 相似文献
15.
Saleh M. Al‐Mousawi Morsy A. El‐Apasery Najat Al‐Kandery Mohamed H. Elnagdi 《Journal of heterocyclic chemistry》2008,45(2):359-364
16.
《化学:亚洲杂志》2017,12(8):920-926
A novel perfluoro‐1,4‐phenylenyl 6H ‐indolo[2,3‐b ]quinoxaline derivative ( TFBIQ ) was designed and synthesized by using a C−H direct arylation method. The optoelectrical properties of the obtained TFBIQ were fully characterized by UV/Vis spectroscopy, photoluminescence spectroscopy, cyclic voltammetry, and a group of Alq3‐based green organic light‐emitting diodes (OLEDs). Device A, which used 0.5 nm‐thick TFBIQ as the interfacial modification layer, exhibited the five best advantages of device performance including a minimum turn‐on voltage as low as 3.1 V, a maximum luminescence intensity as high as 26564 cd m−2, a highest current density value of 348.9 mA cm−2 at a voltage of 11 V, the smallest efficiency roll‐off, as well as the greatest power efficiency of 1.46 lm W−1 relative to all of the other tested devices with thicker TFBIQ and also 10 nm‐thick MoO3 as hole‐injection layers (HILs). As a promising candidate for an organic HIL material, the as‐prepared TFBIQ exhibited a strong thickness effect on the performance of corresponding OLEDs. Furthermore, the theoretical calculated vertical ionization potential of the fluorinated TFBIQ suggests better anti‐oxidation stability than that of the non‐fluorinated structure. 相似文献
17.
Interaction of 3‐(2‐Aminophenyl)‐6‐R1‐1,2,4‐triazin‐5‐ones with Acylating Reagents: An Efficient Method for Preparation of 6‐Substituted 3‐R1‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐ones
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Alexey Yu. Voskoboynik Dmitriy Yu. Scorina Tetiana Yu. Sergeieva Sergiy I. Kovalenko Sergiy I. Okovytyy Irina V. Omelchenko Oleg V. Shishkin 《Journal of heterocyclic chemistry》2016,53(3):776-783
The series of 6‐substituted 3‐R1‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐one was prepared via condensation of 3‐(2‐aminophenyl)‐6‐R1‐1,2,4‐triazin‐5‐ones with acylating reagents. Particularities of 1H NMR spectra have been also discussed based on the comparison of experimental and theoretical results for 3‐methyl‐6‐phenyl‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐one and its 4,3‐isomer. 相似文献
18.
Emin Sarıpınar Süleyman Karataş İlhan Özer İlhan 《Journal of heterocyclic chemistry》2007,44(5):1065-1069
19.
3‐Alkyl/aryl‐3‐ureido‐1H,3H‐quinoline‐2,4‐diones ( 2 ) and 3a‐alkyl/aryl‐9b‐hydroxy‐3,3a,5,9b‐tetrahydro‐1H‐imidazo[4,5‐c]quinoline‐2,4‐diones ( 3 ) react in boiling concentrated HCl to give 5‐alkyl/aryl‐4‐(2‐aminophenyl)‐1,3‐dihydro‐2H‐imidazol‐2‐ones ( 6 ). The same compounds were prepared by the same procedure from 2‐alkyl/aryl‐3‐ureido‐1H‐indoles ( 4 ), which were obtained from the reaction of 3‐alkyl/aryl‐3‐aminoquinoline‐2,4(1H,3H)‐diones ( 1 ) with 1,3‐diphenylurea or by the transformation of 3a‐alkyl/aryl‐9b‐hydroxy‐3,3a,5,9b‐tetrahydro‐1H‐imidazo[4,5‐c]quinoline‐2,4‐diones ( 3 ) and 5‐alkyl/aryl‐4‐(2‐aminophenyl)‐1,3‐dihydro‐2H‐imidazol‐2‐ones ( 6 ) in boiling AcOH. The latter were converted into 1,3‐bis[2‐(2‐oxo‐2,3‐dihydro‐1H‐imidazol‐4‐yl)phenyl]ureas ( 5 ) by treatment with triphosgene. All compounds were characterized by 1H‐ and 13C‐NMR and IR spectroscopy, as well as atmospheric pressure chemical‐ionisation mass spectra. 相似文献
20.
An effective and pragmatic strategy for the synthesis of structurally diverse indolo[2,3‐c]isoquinolin‐5‐ones has been developed via a Rh(III)‐catalyzed C?H activation and [4+2] annulation reaction of N‐methoxybenzamides and 3‐diazoindolin‐2‐imines. The reaction involves the efficient formation of two new (one C?C and one C?N) bonds under operationally simple conditions and has the benefits of a broad substrate scope. 相似文献