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Journal of The Chemical Society C: Organic最新文献

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Pyridazines. Part II. Reaction of polychloropyridazines with trimethylamine 邻二氮杂苯。第二部分。多氯吡嗪与三甲胺的反应
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710001536
R. Fenton, J. K. Landquist, S. Meek
{"title":"Pyridazines. Part II. Reaction of polychloropyridazines with trimethylamine","authors":"R. Fenton, J. K. Landquist, S. Meek","doi":"10.1039/J39710001536","DOIUrl":"https://doi.org/10.1039/J39710001536","url":null,"abstract":"Polychloropyridazines with trimethylamine give trimethylpyridazinylammonium chlorides, and these, with the exception of 5,6-dichloropyridazin-3-ylammonium chloride, undergo demethylation in the reaction mixture at room temperature, affording dimethylaminopyridazine derivatives. The position of substitution is governed by the steric requirements of the quaternary salt. Chloropyrimidines and cyanuric chloride are also dimethylaminated by trimethylamine. The structures of the products were established by reaction with nucleophiles and by hydrogenolysis.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"29 1","pages":"1536-1539"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78214287","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
Isothiazoles. Part XIII. Isothiazole sulphides and sulphones Isothiazoles。十三。异噻唑类硫化物和磺胺类
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000776
M. Caton, G. C. Martin, D. L. Pain
{"title":"Isothiazoles. Part XIII. Isothiazole sulphides and sulphones","authors":"M. Caton, G. C. Martin, D. L. Pain","doi":"10.1039/J39710000776","DOIUrl":"https://doi.org/10.1039/J39710000776","url":null,"abstract":"The synthesis of di-isothiazolyl sulphides and their oxidation to sulphoxides and sulphones are described. Isothiazolylphenyl sulphones are prepared by condensation of sodium benzenesulphinates and 5-bromo-3-methyl-4-nitroisothiazole. None of these compounds possess useful biological properties.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"24 1","pages":"776-780"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78579652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Preparation of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines 2-酰基和2-烷氧羰基-八氢吲哚[2,3-a]喹诺嗪的制备
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000736
M. Allen, A. J. Gaskell, J. Joule
{"title":"Preparation of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines","authors":"M. Allen, A. J. Gaskell, J. Joule","doi":"10.1039/J39710000736","DOIUrl":"https://doi.org/10.1039/J39710000736","url":null,"abstract":"A method for the synthesis of 2-acyl- and 2-alkoxycarbonyl-octahydroindolo[2,3-a]quinolizines is described which involves as a key step the isomerisation of a 4-acyl- or 4-alkoxycarbonyl-1-[2-(indol-3-yl)ethyl]-1,2,3,6-tetra-hydropyridine to a 4-acyl- or 4-alkoxycarbonyl-1-[2-(indol-3-yl)ethyl]-1,2,3,4-tetrahydropyridine (not isolated). This, in turn, in reacting as a cyclic enamine, provides by protonation an electrophilic centre for closure on to the indole α-position. The 4-acyl-1-[2-(indol-3-yl)ethyl]-1,2,3,6-tetrahydropyridines can be cyclised in an alternative manner to give compounds comprising four of the five skeletal rings of the Iboga alkaloids.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"317 1","pages":"736-743"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75446217","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
Reaction of copper(I) acetylides with halogeno-acetylenes 乙酰化铜与卤代乙炔的反应
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000186
R. Curtis, J. A. Taylor
{"title":"Reaction of copper(I) acetylides with halogeno-acetylenes","authors":"R. Curtis, J. A. Taylor","doi":"10.1039/J39710000186","DOIUrl":"https://doi.org/10.1039/J39710000186","url":null,"abstract":"The reaction between the copper(I) derivatives of propyne, ethynylbenzene, 5-ethynyl-2,2′-bithienyl, 3-(tetra-hydropyranyloxy)prop-1-yne, 3,3-diethoxyprop-1-yne, and but-1-yn-3-ol with 3-bromoprop-2-yn-1-ol in pyridine at 35–50° gave a simple synthesis of the corresponding diynols hexa-2,4-diyn-1-ol (III), 5-phenylpenta-2,4-diyn-1-ol (V), 6-(tetrahydropyranyloxy)hexa-2,4-diyn-1-ol, and 6,6-diethoxyhexa-2,4-diyn-1-ol, hepta-2,4-diyn-1,6-diol, and 5-(5-hyoroxypenta-1,3-diynyl)-2,2′-bithienyl, respectively. Oxidation of (III) and (V) with nickel peroxide in benzene followed by deformylation led to the terminal acetylenes penta-1,3-diyne (XIV) and 4-phenylbuta-1,3-diyne, and subsequent coupling of the corresponding copper(I) salt of, e.g., (XIV) with the 3-bromopropynol produced a new homologation sequence for polyacetylenes exemplified by the synthesis of octa-2,4,6-triyn-1-ol.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"39 1","pages":"186-188"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77928842","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 11
Factors which affect the stability of aluminium hydride solutions 影响氢化铝溶液稳定性的因素
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000044
D. C. Ayres, R. Sawdaye
{"title":"Factors which affect the stability of aluminium hydride solutions","authors":"D. C. Ayres, R. Sawdaye","doi":"10.1039/J39710000044","DOIUrl":"https://doi.org/10.1039/J39710000044","url":null,"abstract":"The loss of reducing power of solutions of this reagent in ethers is shown to depend on both aggregation and solvolysis. The former is dominant at higher concentrations and at lower temperatures, whereas the latter controls the rate of inactivation of dilute solutions.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"61 1","pages":"44-46"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73069108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 3
A galactan from onion (Allium cepa Linn.) pectic substance 半乳一种从洋葱(洋葱属葱属植物)果胶物质中提取的半乳
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710001788
S. K. Sen, B. Chatterjee, C. Rao
{"title":"A galactan from onion (Allium cepa Linn.) pectic substance","authors":"S. K. Sen, B. Chatterjee, C. Rao","doi":"10.1039/J39710001788","DOIUrl":"https://doi.org/10.1039/J39710001788","url":null,"abstract":"The pectic substance of onion was treated with the enzyme polygalacturonase and then extracted with 70% ethanol to remove galacturonan and araban components respectively. The resulting material was methylated and fractionated to yield pure methylated galactan which on hydrolysis gave 2,3,4,6-tetra-, 2,3,6-tri-, and 2,3-di-O-methyl-D-galactose. Polysaccharide material containing 91·2% galactose, was isolated by separating the crude pectic substance on a DEAE–cellulose column followed by fractionation. Periodate oxidation studies were carried out on these two galactan-rich fractions. The structure of the repeating unit of galactan is discussed in the light of these results.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"129 1","pages":"1788-1791"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74989886","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 10
Unsaturated nitrogen compounds containing fluorine. Part I. The thermal and photochemical reactions of hexafluoroacetone azine with acetylene and with hydrocarbon terminal olefins 含氟的不饱和氮化合物。第一部分:六氟丙酮azine与乙炔和与烃类末端烯烃的热化学和光化学反应
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710002404
T. Forshaw, A. E. Tipping
{"title":"Unsaturated nitrogen compounds containing fluorine. Part I. The thermal and photochemical reactions of hexafluoroacetone azine with acetylene and with hydrocarbon terminal olefins","authors":"T. Forshaw, A. E. Tipping","doi":"10.1039/J39710002404","DOIUrl":"https://doi.org/10.1039/J39710002404","url":null,"abstract":"Hexafluoroacetone azine reacts with ethylene, with propene, and with but-1-ene at 160—180° to give high yields of the corresponding 1 : 2 adducts, 1,5-diazabicyclo[3,3,0]octanes. Acetylene reacts similarly to give the corresponding 1,5-diazabicyclo[3,3,0]octa-2,6-diene. The olefins also react under photochemical conditions to give the same products, but acetylene does not react. The azine does not react with electron-deficient olefins or acetylenes under comparable conditions. Pyrolysis of the ethylene or propene adducts affords 3,3,3-trifluoro-2-trifluoromethylpropene in high yield; the acetylene adduct gives mainly a mixture of hexafluoroethane and 3,3,3-trifluoropropyne, together with 1,1,1,6,6,6-hexafluoro-2,5-bistrifluoromethylhexa-2,4-diene.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"38 1","pages":"2404-2408"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75261443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 10
Condensed thiophen ring systems. Part VII. Stability of 3-benzo[b]-thienyl-lithium 缩合噻吩环体系。第七部分。3-苯并[b]-噻吩锂的稳定性
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710003447
R. Dickinson, B. Iddon
{"title":"Condensed thiophen ring systems. Part VII. Stability of 3-benzo[b]-thienyl-lithium","authors":"R. Dickinson, B. Iddon","doi":"10.1039/J39710003447","DOIUrl":"https://doi.org/10.1039/J39710003447","url":null,"abstract":"Ring-cleavage reactions of 3-benzo[b]thienyl-lithium (1) and its 2-methyl derivative are reported. When an ethereal solution of compound (1), prepared by treating 3-bromobenzo[b]thiophen with n-butyl-lithium at –70 °C, was kept for 1 h at room temperature prior to treatment of the product with dimethyl sulphate, it gave a mixture of benzo[b]thiophen, 3-bromo-2-methylbenzo[b]thiophen, o-(methylthio)phenylacetylene, and methyl-[o-(methyl-thio)phenyl]acetylene. A similar reaction mixture kept for 18 h at room temperature prior to methylation of the product gave a mixture of benzo[b]thiophen, the two acetylenes obtained before, and methyl -[o-(n-butylthio)-phenyl]acetylene. Methyl-[o-(methylthio)phenyl]acetylene was also obtained as the major product when an ethereal solution of 2-methyl-3-benzo[b]thienyl-lithium was similarly treated (30 min at room temperature). In contrast, when ethereal solutions of compound (1) were kept at room temperature and the products carboxylated instead of methylated, mixtures of benzo[b]thiophen, 3-bromobenzo[b]thiophen-2-carboxylic acid, and benzo[b]-thiophen-2-carboxylic acid were formed. A mechanism is given to account for these results. An unambiguous synthesis of o-(methylthio)phenylacetylene was attempted and a synthesis of methyl 3-bromobenzo[b]thiophen-2-carboxylate is reported. In tetrahydrofuran ring cleavage of compound (1) does not occur but the transmetallation reactions that predominate in this solvent, even at –70 °C, give rise to mixtures of products following either methylation or carboxylation.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"40 1","pages":"3447-3454"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74551336","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 14
Valence-bond isomer chemistry. Part II. Diels–Alder reactions of hexafluorobicyclo[2,2,0]hexa-2,5-diene : pyrrole as a diene 价键异构体化学。第二部分。六氟双环[2,2,0]六-2,5-二烯:吡咯为二烯的diols - alder反应
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000090
M. Barlow, R. Haszeldine, R. Hubbard
{"title":"Valence-bond isomer chemistry. Part II. Diels–Alder reactions of hexafluorobicyclo[2,2,0]hexa-2,5-diene : pyrrole as a diene","authors":"M. Barlow, R. Haszeldine, R. Hubbard","doi":"10.1039/J39710000090","DOIUrl":"https://doi.org/10.1039/J39710000090","url":null,"abstract":"Hexafluorobicyclo[2,2,0]hexa-2,5-diene is an active dienophile in the Diels–Alder reaction, reacting at room temperature with 1,3-diphenylisobenzofuran, cyclopentadiene, furan, pyrrole, αα-dimethylfulvene, cyclohexa-1,3-diene, 2,3-dimethylbuta-1,3-diene, 2-methylbuta-1,3-diene, and buta-1,3-diene to give 1 : 1 adducts, and to give 1 : 2 adducts, except with the least reactive dienes, butadiene and cyclohexadiene. Reaction times vary from a few hours with the most reactive dienes, 1,3-diphenylisobenzofuran and cyclopentadiene, to several months with the least reactive ones, butadiene and cyclohexadiene. It is argued, on the basis of spectroscopic data, that reaction occurs by exo-addition to the bicyclo[2,2,0]hexa-2,5-diene, and by exo-addition to the cyclic dienes. This is rationalized in terms of steric factors operating in the transition state.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"6 1","pages":"90-95"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73170385","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 6
Pyridopyrimidines. Part VII. Reductive ring cleavage of pyrido[3,4-d]pyrimidin-4(3H)-ones with lithium aluminium hydride Pyridopyrimidines。第七部分。吡啶[3,4-d]嘧啶-4(3H)- 1与氢化铝锂的还原环裂解
Journal of The Chemical Society C: Organic Pub Date : 1971-01-01 DOI: 10.1039/J39710000780
I. Gelling, D. Wibberley
{"title":"Pyridopyrimidines. Part VII. Reductive ring cleavage of pyrido[3,4-d]pyrimidin-4(3H)-ones with lithium aluminium hydride","authors":"I. Gelling, D. Wibberley","doi":"10.1039/J39710000780","DOIUrl":"https://doi.org/10.1039/J39710000780","url":null,"abstract":"Treatment of pyrido[3,4-d]pyrimidin-4(3H)-ones with lithium aluminium hydride has been shown to yield 3-amino-4-aminomethylpyridines. A 3-aryl substituent enhanced the rate of this cleavage at the 2,3-position, and 4-anilino-methyl-3-ethylamino-2,6-dimethylpyridine, for example, was isolated in excellent yield from a rapid reduction of 2,6,8-trimethyl-3-phenylpyrido[3,4-d]pyrimidin-4(3H)-one. Pyrido[3,4-d]pyrimidin-4(3H)-ones not bearing a 3-aryl substituent also underwent a reductive cleavage at the 2,3-position but much longer periods of time were required and 3,4-dihydro- and 1,2,3,4-tetrahydropyrido[3,4-d]pyrimidines were additionally obtained.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"30 1","pages":"780-784"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74473752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 7
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