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1.
A. M. El Massry 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5):1143-1155
Reaction of phenylpyruvic acid with semicarbazide afforded 6-benzyl-2H-[1,2,4]triazine-3,5-dione ( 1 ) which upon oxidation with potassium dichromate furnished 6-benzoyl-2H-[1,2,4]triazine-3,5-dione ( 2 ) in good yield. Constructing pyrazolo[3,4-e][1,2,4]triazine system ( 4 ) was achieved by reacting 2 with arylhydrazines in ethanolic solution. However treatment of 2 with the less reactive heteroarylhydrazines gave only the corresponding hydrazones ( 3 ). Attempt for constructing 1,2,4,5,10-pentaaza-dibenzo[a,d]cyclohept-3-one ( 7 ) from 2 was failed and (benzoimidazol-2-yl) [1,2,4] triazine derivative ( 6 ) was the only product. Reaction of 1 with phosphorus pentasulphide afforded compounds 8 and 9 . Compound 8 was transformed to the hydrazino compound 14 , which led to the construction of triazolo[4,3-d] [1,2,4]triazine system. Thus compounds 15 and 16 were obtained by reacting 14 with carbon disulfide or acetic anhydride respectively. Attempt to couple 8 with chloroacetic acid failed, while it's known isomer 10 led to the formation of thiazolo [2,3-c] [1,2,4]triazine derivative ( 13 ). Simple theoretical calculation using AM1 and PM3 semiempirical Hamitonian provided rational ways to correlate the reactivity with structure proposed. 相似文献
2.
Mohamed A. A. Elneairy 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):469-483
Pyridine-2(1H)-thione 5 was synthesized from the reaction of 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) and cynothioacetamide (4). Compound 5 reacted with halogented compounds 6a–e to give 2-S-alkylpyridine derivatives 7a–e, which could be in turn cyclized into the corresponding thieno[2,3-b]-pyridine derivatives 8a–e. Compound 8a reacted with hydrazine hydrate to give 9. The latter compound reacted with acetic anhydride (10a), formic acid (10b), acetic acid, ethyl acetoacetate, and pentane-2,4-dione to give the corresponding pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine 13a,b, pyrazolo[3′,4′:4,5]thieno[3,2-d]pyridine 14 and thieno[2,3-b]-pyridine derivatives 18 and 20, respectively. Alternatively, 8c reacted with 10a,b and nitrous acid to afford the corresponding pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine 24a,b and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine 26 derivatives, respectively. Finally compound 5 reacted with methyl iodide to give 2-methylthiopyridine derivative 27, which could be reacted with hydrazine hydrate to yield the corresponding pyrazolo[3,4-b]-pyridine derivative 29. 相似文献
3.
Fawi M. Abd El Latif Eman A. Ei Rady Mohamed A. Khalil 《Phosphorus, sulfur, and silicon and the related elements》2013,188(10):2497-2505
2-Cyano-2-nitrosomethylbenzthiazole reacts with some active methylene and nucleophile derivatives to yield new fused and isolated polyfunctional pyrazine, -[1,2,4]triazine, -[1,4,5]benzoxadiazepin, -[1,4,5]benzothiadiazepine, [1,4,5]benzotriazepine, -triazole and -triazolo[3,2-c]triazine derivatives in one-pot reaction. The structures were based on IR, MS, and 1 H NMR spectra and elemental data. 相似文献
4.
Noriyuki Hatae Ichiro Suzuki Tominari Choshi Satoshi Hibino Chiaki Okada Eiko Toyota 《Tetrahedron letters》2014
Steric and enthalpic effects of substituents on diene moieties play a crucial role in intramolecular cycloaddition reactions. Allenyl 2-halogenated-3-vinylcyclohex-2-enyl ethers underwent a tandem [4+2] cycloaddition/aromatization reaction to afford the corresponding tetrahydro-3H-naphtho[1,8-bc]furan compound in high yield. 相似文献
5.
Shinji Kitagaki 《Tetrahedron》2006,62(44):10311-10320
Reaction of ene-bis(phosphinylallenes), derived from ene-bis(propargyl alcohols) and chlorodiphenylphosphine, was investigated. Benzene-bridged bis(phosphinylallenes) exclusively gave intramolecular [2+2] cycloadducts in the presence of dimethyl fumarate in sharp contrast to the reaction of benzene-bridged bis(sulfinylallenes), which gave the corresponding [4+2] cycloadducts. On the other hand, substituted ethylene- or five-membered heterocycle-bridged bis(phosphinylallenes) provided [4+2] cycloadducts. Reaction of benzene-bridged diallene bearing both a sulfinyl group and a phosphinyl group on the two allenyl groups was also described. 相似文献
6.
Boris A. Trofimov Lyubov N. Sobenina Igor A. Ushakov Denis N. Tomilin Grigorii G. Alexandrov Oleg A. Dyachenko 《Tetrahedron letters》2010,51(38):5028-5031
The [2+2]-cycloadducts of DDQ and 2-ethynylpyrroles, upon ethanolysis (reflux, 15 min or room temperature, 24 h), rearrange from bicyclo[4.2.0]octadienediones to bicyclo[3.2.0]heptadienone- and cyclobutenyl-dihydrofuranone moieties in 55-83% yields, the former rearrangement being the major direction. Benzoquinone ring cleavage is regioselective to afford mostly bicyclo[3.2.0]heptadienone-pyrrole ensembles (85-90% selectivity) in 39-78% yields. The only exception is when the starting compounds contain an ethoxycarbonyl substituent and the pyrrole counterpart is a 4,5,6,7-tetrahydroindole fragment. In this case, the ratio of the rearrangement products is 1:1.2 in a total yield of 83%. An important feature of the dihydrofuranone pathway rearrangement is its 100% diastereoselectivity. 相似文献
7.
Mohamed A. A. Elneairy Sanaa M. Eldin Mohamed F. M. Attia 《Phosphorus, sulfur, and silicon and the related elements》2013,188(7):1346-1357
Pyridine-2(1H)-thione derivatives 3a,b were synthesized from the reaction of 1-(phenyl-sulfanyl)acetone (1) and cinnnamonitrile derivatives 2a,b. Compounds 3a,b reacted with different halogenated reagents 7a–f to give 2-S-alkylpyridine derivatives 8a–l, which could be, in turn, cyclized into the corresponding thieno[2,3-b]pyridine derivatives 9a–l. Compounds 9d,j reacted with acetic anhydride, formic acid, carbon disulfide, phenyl isothiocyanate, and nitrous acid to yield the corresponding pyrido[3′,2′:4,5]thieno[2,3-d]pyrimidine 12a,b, 15a,b, 17a,b, 20a,b, and pyrido[3′,2′:4,5]thieno[2,3-d][1,2,3]triazinone derivatives 22a,b, respectively. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. 相似文献
8.
Enantiomerically pure (R)-quinuclidine-2-carboxylic acid has been prepared by following two related 7 step synthetic routes in 16% and 19% overall yield, respectively, from a 1,2,4-trisubstituted piperidine that is easily prepared from inexpensive d-mannitol. 相似文献
9.
Guo Qiang HU Wen Long HUANG Hai WANG 《中国化学快报》2005,16(10):1309-1312
6/3-(4-Chlorophenyl)-s-triazolo[3, 4-b][1, 3, 4]thiadiazoles (2,a-e) and (Sa-e) were synthesized respectively by intermolecular cyclization of 5-aryl / 4-chlorophenyl-4-amino-3- mercapto-1, 2, 4-triazoles (la-e) and (4) with 4-chlorobenzoic acid / aryl acids, which were condensed with piperazine under phase transfer catalyst TBAB to yield the corresponding free bases of monopiperazine derivatives and followed to form water-soluble salts (3a-e) and (6a-e) with hydrochloric acid in good yields. The in vitro biological results showed that piperazine group conjugated with the above fused heterocycles played an important role in antibacterial activity. The structures of novel compounds were confirmed by IR, 'H NMR, MS and elemental analysis. 相似文献
10.
The highly reactive 1 : 1 intermediate generated in the reaction between dialkyl acetylenedicarboxylate (=but‐2‐ynedioic acid dialkyl ester) 4 and triphenylphosphine was trapped by 2‐amino‐4‐oxo‐4H‐1‐benzopyran‐3‐carboxaldehydes 5 to yield highly functionalized dialkyl‐1,5‐dihydro‐5‐oxo‐1‐phenyl‐2H‐[1]benzopyrano[2,3‐b]pyridine‐2,3‐dicarboxylates in high yield. 相似文献
11.
A general one-pot synthesis of hydroxylbenzo[d]oxazole-2-aliphatic acid esters and hydroxylbenzo[d]oxazole-2-amino acid esters was successfully achieved in good yield by using Meerwein's reagent. 相似文献
12.
This paper describes a new total synthesis for (S)-2-amino-7-methoxytetralin, (S)-7-MeO-AT, from l-aspartic acid in an overall yield of 10% over nine steps. The major loss was ascribed to a key intramolecular Friedel–Crafts cyclization step, which afforded up to 36% yield. Attempts to perform a Friedel–Crafts cyclization of an intermediate phthalimide protected amino alcohol 13 did not give the desired protected (S)-7-MeO-AT. On the other hand, two new isoindolo[1,2-a]isoquinolinone derivatives 14 and 15, were isolated in 21 and 11% yield, respectively. The yield of 15 was improved to 70%. 相似文献
13.
N-Arylidene-2-aryl-imidazo[1,2-a]azin-3-amines were synthesized via a one-pot, four-component condensation reaction using a 2-aminoazine, toluene-4-sulfonylmethyl isocyanide (TsCH2NC), and two equivalents of readily available aromatic aldehydes. The reaction was performed in diethyl ether as the solvent, with p-toluenesulfonic acid (p-TSA) as the catalyst at reflux temperature. 相似文献
14.
M. Komal Reddy T. Ravinder Reddy K. Raghava Raju 《Phosphorus, sulfur, and silicon and the related elements》2013,188(2):313-318
This article describes the reaction of 3,6-diphenyl-thieno[3,2-b]furan-2,5-dione 1 with different amino acids 2a–j in glacial acetic acid which afforded the 2-(2-(3-hydroxy-5-oxo-4-phenylthiophen-2(5H)-ylidene)-2-phenylacetamido)propanoic acid analogues 3a–j and also describes the reaction of 3,6-diphenyl-thieno[3,2-b]thiophene-2,5-dione 4 with different amino acids 5a–e in acidic medium to give 2-(2-(3-mercapto-5-oxo-4-phenylthiophen-2(5H)-ylidene)-2-phenylacetamido)propanoic acid analogues 6a–e. All the compounds have been screened for their anti-inflammatory activity against the carrageenan induced rat paw edema in albino rats. In the primary screening, some of the compounds exhibited appreciable activity. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. 相似文献
15.
A new catalytic system for enantioselective [2+2]-cycloaddition reaction of 2-methoxycarbonyl-2-cyclopenten-1-one with thioacetylene derivatives is described. The use of a catalytic amount (20-30 mol%) of copper(II) salt with chiral bis-pyridine ligand was found to be effective in promoting the [2+2]-cycloaddition reaction, furnishing the corresponding bicyclic compound in good yield and good enantioselectivity. 相似文献
16.
Chiral nitrogen-containing calix[4]arene was easily synthesized by the reaction of 25,27-di(2-bromoethoxy)- 26,28-dihydroxy-5,11,17,23-tetrakis(t-butyl)calix[4]arene with S-(-)-1-phenylethylamine in excellent yield, and showed good ability to recognize the enantiomers of mandelic acid and 2,3-dibenzoyltartaric acid. This finding has potential application to assay and separation of enantiomers of the carboxylic acids. 相似文献
17.
Andrey B. Koldobskii Ekaterina V. Solodova Ivan A. Godovikov Valery N. Kalinin 《Tetrahedron》2008,64(40):9555-9560
The highly activated acetylenes, ethyl 4-chloro-2-oxobut-3-ynoate and ethyl 4-bromo-2-oxobut-3-ynoate, were prepared from readily available bis(trimethylstannyl)acetylene in two steps with high overall yield. An unusual ability of the former to furnish [2+2]-cycloadducts with 1,1-disubstituted alkenes in the absence of irradiation and catalysts was discovered. The cycloaddition of ethyl 4-chloro-2-oxobut-3-ynoate to the 1,2-disubstituted alkenes was shown to be effectively catalyzed with stannic chloride. 相似文献
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20.
The stereochemistry of syn and anti-forms of bridged bicyclo[3.n.1]-2-ene, tricyclo[7.n.1.0]-2-ene (n=1-3) and bicyclo[4.3.1]dec-7-ene derivatives can be assigned from the 13C chemical shift difference of the double bond. Both syn-9-R-bicyclo[3.3.1]non-2-enes and syn-13-R-tricyclo[7.3.1.02,7]tridec-2(7)-enes have a large shielding difference between sp2 carbons, while the corresponding anti-forms have a smaller one. In contrast, 8-R-bicyclo[3.2.1]oct-2-enes and 12-R-tricyclo[7.2.1.02,7]dodec-2(7)-enes have an inverse correlation. The reason of this specificity is the influence of the γ-gauche effect on the chemical shift of C(2) atom. The GIAO theory has been applied to investigate the 13C chemical shifts. The conformational equilibrium in the formamide group of 13-formylamino-tricyclo[7.3.1.02,7]tridec-2(7)-enes has been studied. 相似文献