{"title":"Approaches to heterocyclic analogues of biphenylene. Part I. The reaction of 5,6-diaryl-2,3-dihydropyrazines with alcoholic alkali","authors":"P. England, R. McDougall","doi":"10.1039/J39710002685","DOIUrl":"https://doi.org/10.1039/J39710002685","url":null,"abstract":"2,3-Dihydro-5,6-diphenylpyrazine reacts with alcoholic alkali to form 2,3-diphenylpyrazine and 5,5′,6,6′-tetraphenyl-2,2′-bipyrazinyl, not 2,3,6,7-tetraphenyl-1,4,5,8-tetra-azabiphenylene. 2,3-Dihydro-5,6-bis-(p-methoxy-phenyl)pyrazine undergoes an analogous reaction, but 2,3-dihydro-5,6-bis-(p-nitrophenyl)pyrazine yields only an apparently polymeric material. The reaction of pp′-dinitrobibenzoyl with ethylenediamine produces not only 2,3-dihydro-5,6-bis-(p-nitrophenyl)pyrazine, but also NN′-bis-(p-nitrobenzoyl)ethylenediamine.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"13 1","pages":"2685-2689"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72719932","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}
{"title":"Propyl homologue of tetrahydrocannabinol: its isolation from Cannabis, properties, and synthesis","authors":"E. Gill","doi":"10.1039/J39710000579","DOIUrl":"https://doi.org/10.1039/J39710000579","url":null,"abstract":"The n-propyl homologue of Δ1-tetrahydrocannabinol (Δ1-THC) has been isolated from Cannabis sativa L. The structure of the compound was deduced by i.r., n.m.r., and mass spectroscopy, and was confirmed by synthesis. It has only one-fifth of the activity of Δ1-THC in the mouse catalepsy test, and although present in amounts comparable to Δ1-THC it probably makes only a small contribution to the effects produced by the consumption of crude cannabis.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"66 1","pages":"579-582"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72648589","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}
T. Kametani, C. Seino, K. Yamaki, S. Shibuya*, K. Fukumoto*, K. Kigasawa, F. Satoh, M. Hiiragi, T. Hayasaka
{"title":"Studies on the syntheses of heterocyclic compounds. Part CCCLXXXVI. Alternative total syntheses of galanthamine and N-benzylgalanthamine iodide","authors":"T. Kametani, C. Seino, K. Yamaki, S. Shibuya*, K. Fukumoto*, K. Kigasawa, F. Satoh, M. Hiiragi, T. Hayasaka","doi":"10.1039/J39710001043","DOIUrl":"https://doi.org/10.1039/J39710001043","url":null,"abstract":"Alternative total syntheses of galanthamine (Ia) and N-benzylgalanthamine iodide (VIa) were carried out by phenolic oxidative reactions of the corresponding amides (IIIf and e). Both (–)-and (±)-galanthamine showed analgesic activity comparable to that of morphine.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"3 1","pages":"1043-1047"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73573629","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}
{"title":"trans-Cycloalkenes. Part III. Stereochemistry and mechanism of some reactions of diastereoisomeric 3-substituted trans-cyclo-octenes","authors":"G. H. Whitham, M. Wright","doi":"10.1039/J39710000891","DOIUrl":"https://doi.org/10.1039/J39710000891","url":null,"abstract":"Three types of process are described: (i) the stereospecific addition of acetic acid to (1RS,2RS)-trans-cyclo-oct-2-enyl acetate to give cis-cyclo-octane-1,3-diol diacetate, (ii) the reaction of (1RS,2RS)- and (1SR,2RS)-trans-cyclo-oct-2-enyl methyl ethers with n-butyl-lithium to give (1RS,3RS)-3-butyl-trans-cyclo-oct-1-ene and 3-butyl-cis-cyclo-oct-1-ene, respectively, and (iii) the thermal interconversion of the diastereoisomeric acetates at 167° to give an equilibrium mixture comprising 84% of the (1RS,2RS)- and 16% of the (1SR,2RS)-form.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"20 1","pages":"891-896"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74039132","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}
{"title":"Studies on the syntheses of heterocyclic compounds. Part CDXXI. General synthesis of 7,8-dioxygenated 1-benzyl-1,2,3,4-tetrahydroisoquinolines and elucidation of the structure of caseadine","authors":"T. Kametani, T. Nakano, K. Shishido, K. Fukumoto*","doi":"10.1039/J39710003350","DOIUrl":"https://doi.org/10.1039/J39710003350","url":null,"abstract":"Bischler–Napieralski reactions of the phenolic bromo-amides (11c and d)[prepared by condensation of 5-benzyloxy-2-bromo-4-methoxyphenethylamine (9) with 3,4-dimethoxy-(10a) and 3,4-methylenedioxy-phenacetyl chloride (10b) followed by debenzylation] and reduction of the resultant benzyldihydroisoquinolines (12a and b) gave the 1-benzyl-5-bromo-1,2,3,4-tetrahydro-8-hydroxy-7-methoxyisoquinolines (13a and b). The former (13a) was converted into 1-hydroxy-2,10,11-trimethoxyberbine (3), which was different from caseadine.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"40 1","pages":"3350-3354"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79295219","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}
{"title":"Preparation and deamination of cyclohex-1-enyl- and cyclohexa-1,4-dienyl-methylamine","authors":"K. Stapleford","doi":"10.1039/J39710002580","DOIUrl":"https://doi.org/10.1039/J39710002580","url":null,"abstract":"The rearranged alcohol from the deamination of cyclohex-1-enylmethylamine is 2-methylenecyclohexanol, the product of an allylic rearrangement, and not the ring-expanded alcohol previously reported. An analogous reaction has been shown to take place with cyclohexa-1,4-dienylmethylamine.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"36 1","pages":"2580-2582"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84214372","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}
{"title":"Thermal reactions of N-(diphenylmethylene)methylthiomethylamine N-oxide","authors":"I. W. Jones, D. Kerr, D. Wilson","doi":"10.1039/J39710002595","DOIUrl":"https://doi.org/10.1039/J39710002595","url":null,"abstract":"The title compound, when heated both neat and in solution, forms O-(methylthiomethyl)benzophenone oxime, benzophenone, its oxime, dimethylthiomethane, dimethyl disulphide, and OO′-methylenebis(benzophenone oxime). Mechanisms for these reactions are discussed.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"9 1","pages":"2595-2598"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84587597","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}
T. Kametani, S. Noguchi, I. Agata, T. Aono, K. Kigasawa, M. Hiiragi, T. Hayasaka, O. Kusama
{"title":"Benzyne reaction. Part X. The benzyne reaction of ortho-substituted halogenobenzenes with cyclohexanone in secondary cyclic amines or in organic solvents","authors":"T. Kametani, S. Noguchi, I. Agata, T. Aono, K. Kigasawa, M. Hiiragi, T. Hayasaka, O. Kusama","doi":"10.1039/J39710001047","DOIUrl":"https://doi.org/10.1039/J39710001047","url":null,"abstract":"2-Arylcyclohexanones have been synthesised by the benzyne reaction of o-substituted halogenobenzenes with cyclohexanone or its enamine in the presence of sodium amide in tetrahydrofuran or in secondary cyclic amines.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"41 1","pages":"1047-1050"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84964726","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}
{"title":"Reactions of carbonyl compounds with tervalent phosphorus reagents. Part I. Cyclopentadienones","authors":"J. Miller, G. Stevenson, B. C. Williams","doi":"10.1039/J39710002714","DOIUrl":"https://doi.org/10.1039/J39710002714","url":null,"abstract":"Tetracyclone and 2-methyl-3,4,5-triphenylcyclopentadienone react with diphenylphosphine oxide and with dimethyl phosphonate to produce a series of 1 : 1 adducts, in which the phosphorus is attached to the α-carbon of the ketones. In addition, dimethyl phosphonate forms adducts resulting from reaction at the carbonyl group of tetracyclone. Detailed physical evidence for the structures of these adducts is presented, and the factors which control their formation are discussed.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"44 1","pages":"2714-2720"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85334179","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}
{"title":"Reactions of 2,2-dialkyl-1,2-dihydroquinolines. Part VI. Further bromination studies","authors":"J. P. Brown, O. Meth–Cohn","doi":"10.1039/J39710003631","DOIUrl":"https://doi.org/10.1039/J39710003631","url":null,"abstract":"The product obtained by tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in methanol described by Cliffe is not identical with 3,6,8-tribromo-4-bromomethyl-1,2-dihydro-2,2-dimethylquinoline, the tetrabromination product obtained in chloroform. It has been identified as the isomeric compound 3,6,8-tribromo-4-bromomethylene-1,2,3,4-tetrahydro-2,2-dimethylquinoline. This reacts with aqueous ethanolic alkali to yield an unusual fused aziridine. Further bromination, or nitration, yields dihydroquinolines, accompanied in the former case by a product of oxidative dimerisation which is also the main product of attempted tetrabromination of 1,2-dihydro-2,2,4-trimethylquinoline in sulphuric acid.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"55 1","pages":"3631-3634"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85393533","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}