Pub Date : 2003-06-01DOI: 10.1080/0278611031000104961
A. Demenev, L. Sobenina, A. Mikhaleva, B. Trofimov
New 2-(1-alkylthio-2-dicyanoethenyl)pyrroles or 2-(1-alkylthio-2-cyano-2-carbamoylethenyl)pyrroles of Z-configuration have been synthesized in 58-69% yields by the reaction of pyrrole-2-carbodithioates with CH-acids (malononitrile, cyanoacetamide) in KOH-DMSO. Condensation of ethyl 4,5,6,7-tetrahydroindole-2-carbodithioate with ethyl benzyl malonate affords a mixture (1 : 2) of 1-ethylthio-2-benzyloxycarbonyl-4,5,6,7-tetrahydrocyclohexa[c]pyrrolizine-3-one and 1-ethylthio-2-ethoxycarbonyl-4,5,6,7-tetrahydrocyclohexa[c]pyrrolizine-3-one.
{"title":"Reaction of pyrrole-2-carbodithioates with CH-acids: Stereospecific synthesis of new functional 2-vinylpyrroles","authors":"A. Demenev, L. Sobenina, A. Mikhaleva, B. Trofimov","doi":"10.1080/0278611031000104961","DOIUrl":"https://doi.org/10.1080/0278611031000104961","url":null,"abstract":"New 2-(1-alkylthio-2-dicyanoethenyl)pyrroles or 2-(1-alkylthio-2-cyano-2-carbamoylethenyl)pyrroles of Z-configuration have been synthesized in 58-69% yields by the reaction of pyrrole-2-carbodithioates with CH-acids (malononitrile, cyanoacetamide) in KOH-DMSO. Condensation of ethyl 4,5,6,7-tetrahydroindole-2-carbodithioate with ethyl benzyl malonate affords a mixture (1 : 2) of 1-ethylthio-2-benzyloxycarbonyl-4,5,6,7-tetrahydrocyclohexa[c]pyrrolizine-3-one and 1-ethylthio-2-ethoxycarbonyl-4,5,6,7-tetrahydrocyclohexa[c]pyrrolizine-3-one.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79647848","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}
Pub Date : 2003-06-01DOI: 10.1080/0278611031000095331
S. El-Desoky, S. Bondock, H. Etman, A. Fadda, M. Metwally
Condensation of 1,3-thiazolidinone derivatives 1a-c with different aromatic aldehydes and/or aryldiazonium chlorides gave the corresponding arylidenes 2-10 and arylazo-1,3-thiazolidinones 12-20. Bromination of 12 resulted in the formation of dibromo derivative 21. Treatment of 1a-c with HCHO-piperidine gave the Mannich adduct 24. Compound 1a was hydroxymethylated, oxidized and formylated to yield the products 25-28. The structures of the new products were confirmed by spectral and analytical methods.
{"title":"Synthesis of some new thiazole derivatives of pharmaceutical interest","authors":"S. El-Desoky, S. Bondock, H. Etman, A. Fadda, M. Metwally","doi":"10.1080/0278611031000095331","DOIUrl":"https://doi.org/10.1080/0278611031000095331","url":null,"abstract":"Condensation of 1,3-thiazolidinone derivatives 1a-c with different aromatic aldehydes and/or aryldiazonium chlorides gave the corresponding arylidenes 2-10 and arylazo-1,3-thiazolidinones 12-20. Bromination of 12 resulted in the formation of dibromo derivative 21. Treatment of 1a-c with HCHO-piperidine gave the Mannich adduct 24. Compound 1a was hydroxymethylated, oxidized and formylated to yield the products 25-28. The structures of the new products were confirmed by spectral and analytical methods.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78801297","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}
Pub Date : 2003-06-01DOI: 10.1080/0278611031000104989
I. Forristal, K. Lawson, C. Rayner
The stereoselective conjugate addition of thiolate nucleophiles to γ-hydroxy-α,β-unsaturated sulfoxides and sulfones is reported. Moderate to good levels of diastereoselectivity are observed, with the two stereocontrolling elements, the hydroxyl group and the sulfoxide, showing reinforcing and nonreinforcing control of stereoselectivity, depending on their relative configuration.
{"title":"Stereoselective conjugate addition of thiolate nucleophiles to (E)-?-hydroxy-a,ß-unsaturated sulfoxides and sulfones","authors":"I. Forristal, K. Lawson, C. Rayner","doi":"10.1080/0278611031000104989","DOIUrl":"https://doi.org/10.1080/0278611031000104989","url":null,"abstract":"The stereoselective conjugate addition of thiolate nucleophiles to γ-hydroxy-α,β-unsaturated sulfoxides and sulfones is reported. Moderate to good levels of diastereoselectivity are observed, with the two stereocontrolling elements, the hydroxyl group and the sulfoxide, showing reinforcing and nonreinforcing control of stereoselectivity, depending on their relative configuration.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89318778","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}
Pub Date : 2003-06-01DOI: 10.1080/0278611031000095322
M. Metwally, E. Abdel‐Latif, F. A. Amer
Thiocarbamoyl derivatives (2a-c) were prepared in a good yield by a modified method. Their behavior toward aromatic diazonium salts, hydrazine hydrate and chloroacetyl chloride were investigated. The structures of the ring systems have been confirmed by analytical and spectral methods.
{"title":"Synthesis and reactions of some thiocarbamoyl derivatives","authors":"M. Metwally, E. Abdel‐Latif, F. A. Amer","doi":"10.1080/0278611031000095322","DOIUrl":"https://doi.org/10.1080/0278611031000095322","url":null,"abstract":"Thiocarbamoyl derivatives (2a-c) were prepared in a good yield by a modified method. Their behavior toward aromatic diazonium salts, hydrazine hydrate and chloroacetyl chloride were investigated. The structures of the ring systems have been confirmed by analytical and spectral methods.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83197053","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}
Pub Date : 2003-06-01DOI: 10.1080/0278611031000107111
V. Vasin, I. Bolusheva, V. Razin
The UV-initiated addition of bromomethane sulfonyl bromide to phenylacetylene (quartz test tube, CH2Cl2, 20 °C) gives bromomethyl (E)-2-bromo-2-phenylethenyl sulfone. In a similar reaction with styrene, bromomethyl 2-bromo-2-phenylethyl sulfone is formed. Subsequent dehydrobromination of this adduct (Na2CO3 in aqueous dioxane, 20 °C) gives bromomethyl (E)-2-phenylethenyl sulfone, which is transformed by bromination-dehydrobromination (Br2 in CCl4 at 20 °C, then Na2CO3 in aqueous dioxane, 50 °C) into bromomethyl (Z)-1-bromo-2-phenylethenyl sulfone. Upon heating in methanol in the presence of sodium methoxide, the unsaturated sulfones enter the Michael-induced Ramberg-Bäcklund reaction. Monobromo-substituted derivative transforms into 1-(1-methoxy-2-propenyl)benzene. Dibromosubstituted derivatives give 1-(1,1-dimethoxy-2-propenyl)benzene via intermediate formation of bromomethyl 2-methoxy-2-phenylethenyl sulfone through elimination-addition or vinylic substitution.
{"title":"Bromomethyl ß-styryl and ß-bromostyryl sulfones in the Michael-induced Ramberg-Bäcklund reaction","authors":"V. Vasin, I. Bolusheva, V. Razin","doi":"10.1080/0278611031000107111","DOIUrl":"https://doi.org/10.1080/0278611031000107111","url":null,"abstract":"The UV-initiated addition of bromomethane sulfonyl bromide to phenylacetylene (quartz test tube, CH2Cl2, 20 °C) gives bromomethyl (E)-2-bromo-2-phenylethenyl sulfone. In a similar reaction with styrene, bromomethyl 2-bromo-2-phenylethyl sulfone is formed. Subsequent dehydrobromination of this adduct (Na2CO3 in aqueous dioxane, 20 °C) gives bromomethyl (E)-2-phenylethenyl sulfone, which is transformed by bromination-dehydrobromination (Br2 in CCl4 at 20 °C, then Na2CO3 in aqueous dioxane, 50 °C) into bromomethyl (Z)-1-bromo-2-phenylethenyl sulfone. Upon heating in methanol in the presence of sodium methoxide, the unsaturated sulfones enter the Michael-induced Ramberg-Bäcklund reaction. Monobromo-substituted derivative transforms into 1-(1-methoxy-2-propenyl)benzene. Dibromosubstituted derivatives give 1-(1,1-dimethoxy-2-propenyl)benzene via intermediate formation of bromomethyl 2-methoxy-2-phenylethenyl sulfone through elimination-addition or vinylic substitution.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89833493","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}
Pub Date : 2003-06-01DOI: 10.1080/0278611031000138027
H. Xi, Xiaoqiang Sun, Yang Yang, Q. Meng, Yi Pan, Hongwen Hu
A series of monofunctionalized hydroquinol oligoether chains terminated by thiols were designed and synthesized from unsymmetric starting materials in good yields by multi-procedure reactions at mild temperatures. In a thermodynamically controlled self-assembly process, several pseudorotaxanes based on the π-electron-rich hydroquinol oligoether thiols and π-electron deficient cyclobis(paraquat-p-phenylene) (CPQT) were formed. Furthermore, a gold cation was added to the self-assembly systems and 1H NMR studies on the thiol/Au systems revealed that Au3+ is an efficient terminal stopper of pseudorotaxanes or rotaxanes; the pseudorotaxane can be unthreaded or rethreaded at different temperatures. These could be a basis for the future development of mechanoelectrical and photoelectrical communication systems, and devices capable of storing and processing information.
{"title":"Synthesis of o-?-mercapto [poly(ethyleneoxy)]-o'-alkylhydroquinol derivatives and formation of novel pseudorotaxanes","authors":"H. Xi, Xiaoqiang Sun, Yang Yang, Q. Meng, Yi Pan, Hongwen Hu","doi":"10.1080/0278611031000138027","DOIUrl":"https://doi.org/10.1080/0278611031000138027","url":null,"abstract":"A series of monofunctionalized hydroquinol oligoether chains terminated by thiols were designed and synthesized from unsymmetric starting materials in good yields by multi-procedure reactions at mild temperatures. In a thermodynamically controlled self-assembly process, several pseudorotaxanes based on the π-electron-rich hydroquinol oligoether thiols and π-electron deficient cyclobis(paraquat-p-phenylene) (CPQT) were formed. Furthermore, a gold cation was added to the self-assembly systems and 1H NMR studies on the thiol/Au systems revealed that Au3+ is an efficient terminal stopper of pseudorotaxanes or rotaxanes; the pseudorotaxane can be unthreaded or rethreaded at different temperatures. These could be a basis for the future development of mechanoelectrical and photoelectrical communication systems, and devices capable of storing and processing information.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88316214","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}
Pub Date : 2003-04-01DOI: 10.1080/0278611031000095368
A. V. Martynov, N. Makhaeva, V. Potapov, S. Amosova
Different approaches to the synthesis of ω-(organylchalcogeno)alkyl phosphonates were examined. It is established that diethyl 2-(organylseleno (telluro))ethyl- and 4-(organyl-thio(seleno, telluro))butyl phosphonates are formed by nucleophilic substitution of bromine in diethyl 2-bromoethyl- and 4-bromobutyl phosphonates with chalcogenolate anions generated from the corresponding diorganyl dichalcogenides. The 1H and 31P NMR spectra of these phosphonates are discussed.
{"title":"Terminal organylchalcogenoalkyl phosphonates","authors":"A. V. Martynov, N. Makhaeva, V. Potapov, S. Amosova","doi":"10.1080/0278611031000095368","DOIUrl":"https://doi.org/10.1080/0278611031000095368","url":null,"abstract":"Different approaches to the synthesis of ω-(organylchalcogeno)alkyl phosphonates were examined. It is established that diethyl 2-(organylseleno (telluro))ethyl- and 4-(organyl-thio(seleno, telluro))butyl phosphonates are formed by nucleophilic substitution of bromine in diethyl 2-bromoethyl- and 4-bromobutyl phosphonates with chalcogenolate anions generated from the corresponding diorganyl dichalcogenides. The 1H and 31P NMR spectra of these phosphonates are discussed.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82363298","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}
Pub Date : 2003-04-01DOI: 10.1080/0278611031000095340
A. Hajipour, S. Mallakpour, I. Mohammadpoor‐Baltork, H. Adibi, A. Ruoho
Alumina-supported potassium permanganate was found to be an efficient and mild reagent for the dethioacetalization of thioacetals 1 to the corresponding carbonyl compounds 2 under solvent-free conditions.
氧化铝负载高锰酸钾在无溶剂条件下将硫缩醛1脱硫缩醛化为相应的羰基化合物2，是一种高效且温和的试剂。
{"title":"Alumina-supported potassium permanganate: A mild, inexpensive and efficient reagent for solvent-free deprotection of thioacetals","authors":"A. Hajipour, S. Mallakpour, I. Mohammadpoor‐Baltork, H. Adibi, A. Ruoho","doi":"10.1080/0278611031000095340","DOIUrl":"https://doi.org/10.1080/0278611031000095340","url":null,"abstract":"Alumina-supported potassium permanganate was found to be an efficient and mild reagent for the dethioacetalization of thioacetals 1 to the corresponding carbonyl compounds 2 under solvent-free conditions.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76352215","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}
Pub Date : 2003-04-01DOI: 10.1080/0278611031000112656
A. Hajipour, A. Ruoho
This paper describes an efficient and easy method for oxidation of sulfides 1 to their corresponding sulfoxides 2 with benzyltriphenylphosphonium chlorochromate (BTPPCC) in high yields under non-aqueous conditions.
{"title":"Benzyltriphenylphosphonium chlorochromate (btppcc): An efficient and novel reagent for oxidation of sulfides to the corresponding sulfoxides under non-aqueous conditions","authors":"A. Hajipour, A. Ruoho","doi":"10.1080/0278611031000112656","DOIUrl":"https://doi.org/10.1080/0278611031000112656","url":null,"abstract":"This paper describes an efficient and easy method for oxidation of sulfides 1 to their corresponding sulfoxides 2 with benzyltriphenylphosphonium chlorochromate (BTPPCC) in high yields under non-aqueous conditions.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89532162","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}
Pub Date : 2003-04-01DOI: 10.1080/0278611021000048703
A. Shaabani, Donald G. Lee
Alkyl and aryl sulfides can be oxidized under mild, solvent-free conditions with good selectivity. If the oxidant is a mixture of sodium bromate and cation exchange resin, the products are sulfoxides; if it is a mixture of permanganate and copper sulfate pentahydrate, the products are sulfones. The procedures are experimentally simple and the products, obtained in nearly quantitative yields, are easily separated and purified.
{"title":"Selective oxidation of sulfides under solvent-free conditions","authors":"A. Shaabani, Donald G. Lee","doi":"10.1080/0278611021000048703","DOIUrl":"https://doi.org/10.1080/0278611021000048703","url":null,"abstract":"Alkyl and aryl sulfides can be oxidized under mild, solvent-free conditions with good selectivity. If the oxidant is a mixture of sodium bromate and cation exchange resin, the products are sulfoxides; if it is a mixture of permanganate and copper sulfate pentahydrate, the products are sulfones. The procedures are experimentally simple and the products, obtained in nearly quantitative yields, are easily separated and purified.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74400131","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}
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