Reaction of 3-amino-2-ethoxycarbonylindole ( 1 ) with per- O -acetyl-sugar isothiocyanates 2a-c gave the corresponding glycopyranosyl thioureas 3a-c . The N -nucleosides analogues 3-(per- O -acetyl- β -D-glycopyranosyl)-2-thioxo-5H-3, 4-dihydropyrimido [5,4-b] indol- 4 -one 4a-c were obtained by cyclization of 3a-c in the presence of ZnCl2. Deacetylation of 4a-c with sodium methoxide in methanol yielded the free nucleoside derivatives 5a-c . Alkylation of 5a,b with methyl iodide and benzyl bromide gave good yields of the corresponding 2-methylthio 6a,b and the 2-benzylthio 6c,d analogues. The 2-methylsulfonyl compounds 7a,b were obtained from the corresponding 2-methylthio compounds 6a,b by oxidation with m -chloroperoxybenzoic acid.
3-氨基-2-乙氧基羰基吲哚(1)与每- O -乙酰基糖异硫氰酸酯2a-c反应得到相应的甘氨酰硫脲3a-c。在ZnCl2的存在下，将3a-c环化，得到了N -核苷类似物3-(per- O -乙酰基- β -d -glycopyranosyl)-2-硫氧基- 5h - 3,4 -二氢嘧啶[5,4-b]吲哚- 4- 1 4a-c。4a-c与甲氧基钠在甲醇中脱乙酰化，得到游离核苷衍生物5a-c。5a,b与碘化甲酯和苄基溴的烷基化反应得到了相应的2-甲基硫代6a,b和2-甲基硫代6c,d类似物的良好产率。由相应的2-甲基硫代化合物6a、b与间氯过氧苯甲酸氧化得到2-甲基磺酰基化合物7a、b。
{"title":"A convenient synthesis of novel nucleosides of 2-thioxo-5h-3,4-dihydropyrimido[5,4-b]indol-4-one","authors":"M. Saleh","doi":"10.1080/02786110215845","DOIUrl":"https://doi.org/10.1080/02786110215845","url":null,"abstract":"Reaction of 3-amino-2-ethoxycarbonylindole ( 1 ) with per- O -acetyl-sugar isothiocyanates 2a-c gave the corresponding glycopyranosyl thioureas 3a-c . The N -nucleosides analogues 3-(per- O -acetyl- β -D-glycopyranosyl)-2-thioxo-5H-3, 4-dihydropyrimido [5,4-b] indol- 4 -one 4a-c were obtained by cyclization of 3a-c in the presence of ZnCl2. Deacetylation of 4a-c with sodium methoxide in methanol yielded the free nucleoside derivatives 5a-c . Alkylation of 5a,b with methyl iodide and benzyl bromide gave good yields of the corresponding 2-methylthio 6a,b and the 2-benzylthio 6c,d analogues. The 2-methylsulfonyl compounds 7a,b were obtained from the corresponding 2-methylthio compounds 6a,b by oxidation with m -chloroperoxybenzoic acid.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"149 1","pages":"235 - 245"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86131181","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}
( E )-Stereoisomers of imidazo[1,2- a ]pyridine gem -amido vinyl sulfoxides and vinyl sulfones are efficiently prepared by condensation of N , N -diethylphenylsulfinyl or z N , N -diethylphenyl- sulfonylacetamide with imidazo[1,2- a ]pyridine-2-carbaldehyde in the presence of NEt 3 .
在NEt 3存在下，用N, N -二乙基苯基亚砜或z N, N -二乙基苯基磺酰乙酰胺与咪唑[1,2- a]吡啶-2-乙醛缩合制备了咪唑[1,2- a]吡啶-2-乙醛立体异构体和乙烯基砜。
{"title":"Synthesis of Imidazo[1,2- a ] Pyridine Gem -Amido Vinyl Sulfides, Vinyl Sulfoxides And Vinyl Sulfones. Influence of the Degree of Oxidation of the Sulfur on the Stereoselectivity of the Reaction","authors":"S. Céard, M. Vivier, D. Roche, M. Madesclaire","doi":"10.1080/02786110210633","DOIUrl":"https://doi.org/10.1080/02786110210633","url":null,"abstract":"( E )-Stereoisomers of imidazo[1,2- a ]pyridine gem -amido vinyl sulfoxides and vinyl sulfones are efficiently prepared by condensation of N , N -diethylphenylsulfinyl or z N , N -diethylphenyl- sulfonylacetamide with imidazo[1,2- a ]pyridine-2-carbaldehyde in the presence of NEt 3 .","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"3 1","pages":"15 - 20"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91313074","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}
High-level ab initio calculations predicted the strained three-membered trithia[1.1.1]propellane 1a (X=Y=Z=S) to be a tightly-bound molecule which should be experimentally accessible. In analogy to the successful synthesis of'the [1.1.1] propellane, our synthesis strategy focused on the attempted preparation of 1,3-dihalo-trithia-bicyclo[1.1.1] pentanes 2 , to serve as a precursor for the target molecule. However, 1a proved to be unattainable via the planned strategy beyond the stage of the readily synthesized, substituted 1,3-dithietanes 3 , due to the inaccessibility of 2 from the latter. The successfully synthesized 1,3-dithietanes 5c,d are expected to provide 2 , the key precursor of 1 via 1,3-dihalogenation-dehalogenation.
{"title":"In pursuit of the elusive trithia[1.1.1]propellane: Synthesis of potential 1,3-dithietane precursors","authors":"U. Zoller, Fayun Chen","doi":"10.1080/02786110212860","DOIUrl":"https://doi.org/10.1080/02786110212860","url":null,"abstract":"High-level ab initio calculations predicted the strained three-membered trithia[1.1.1]propellane 1a (X=Y=Z=S) to be a tightly-bound molecule which should be experimentally accessible. In analogy to the successful synthesis of'the [1.1.1] propellane, our synthesis strategy focused on the attempted preparation of 1,3-dihalo-trithia-bicyclo[1.1.1] pentanes 2 , to serve as a precursor for the target molecule. However, 1a proved to be unattainable via the planned strategy beyond the stage of the readily synthesized, substituted 1,3-dithietanes 3 , due to the inaccessibility of 2 from the latter. The successfully synthesized 1,3-dithietanes 5c,d are expected to provide 2 , the key precursor of 1 via 1,3-dihalogenation-dehalogenation.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"25 1","pages":"115 - 121"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82177468","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}
B. Trofimov, L. Parshina, N. Gusarova, N. Ivanova, G. Myachina, I. Kovalev, T. Skotheim
Catalytic copolymerization of sulfur with 5-vinylbicyclo[2.2.1]hept-2-ene or tricyclo[5.2.1.0 2.6 ]deca-3,8-diene (sulfur:diene ratio=20:1) at 170 v °C in bulk or decalin in the presence of 1,4-diazabicyclo[2.2.2]octane or N,N,N,N-tetramethylethylenediamine in combination with CoCl 2 - 6H 2 O or Cu(acac) 2 occurs at two dienic double bonds to form partially cross-linked copolymers stable up to 200 v °C (DSC/TGA). Preliminary evaluation of the specific discharge capacity of cathodes made using the above copolymers in model lithium button cells gives 670-970 and 300-330 v mA - h - g m 1 in the 1st and 50th cycles, respectively.
硫与5-乙烯基双环[2.2.1]庚-2-烯或三环[5.2.1.0 2.6]癸-3,8-二烯(硫:二烯比=20:1)在170 v°C下催化共聚，或在1,4-重氮双环[2.2.2]辛烷或N,N,N,N-四甲基乙二胺与CoCl 2- 6h2o或Cu(acac) 2结合的情况下，在两个二烯双键上形成部分交联共聚物，稳定至200 v°C (DSC/TGA)。用上述共聚物制成的阴极在模型锂扣式电池中，在第一次和第50次循环时的比放电容量分别为670-970和300-330 v mA - h - g - m1。
{"title":"Sulfur-rich copolymers of sulfur with 5-vinylbicyclo[2.2.1]hept-2-ene and tricyclo[5.2.1.0 2.6]deca-3,8-diene as prospective cathode materials for lithium cells","authors":"B. Trofimov, L. Parshina, N. Gusarova, N. Ivanova, G. Myachina, I. Kovalev, T. Skotheim","doi":"10.1080/02786110214494","DOIUrl":"https://doi.org/10.1080/02786110214494","url":null,"abstract":"Catalytic copolymerization of sulfur with 5-vinylbicyclo[2.2.1]hept-2-ene or tricyclo[5.2.1.0 2.6 ]deca-3,8-diene (sulfur:diene ratio=20:1) at 170 v °C in bulk or decalin in the presence of 1,4-diazabicyclo[2.2.2]octane or N,N,N,N-tetramethylethylenediamine in combination with CoCl 2 - 6H 2 O or Cu(acac) 2 occurs at two dienic double bonds to form partially cross-linked copolymers stable up to 200 v °C (DSC/TGA). Preliminary evaluation of the specific discharge capacity of cathodes made using the above copolymers in model lithium button cells gives 670-970 and 300-330 v mA - h - g m 1 in the 1st and 50th cycles, respectively.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"32 1","pages":"219 - 227"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84033630","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}
K. Prabakaran, S. Pyne, B. Skelton, Allan H. White
The crystal structure of (1 R ,2 S ,5 R )-menthyl ( S )-2-methoxy-1-naphthalene sulfinate (C 21 H 27 O 3 S) is reported, thus confirming the absolute stereochemistry of this synthetically important molecule.
{"title":"Crystal Structure of (1 R ,2 S ,5 R )-Menthyl ( S )-2-Methoxy-Naphthalene-1-Sulfinate","authors":"K. Prabakaran, S. Pyne, B. Skelton, Allan H. White","doi":"10.1080/02786110211431","DOIUrl":"https://doi.org/10.1080/02786110211431","url":null,"abstract":"The crystal structure of (1 R ,2 S ,5 R )-menthyl ( S )-2-methoxy-1-naphthalene sulfinate (C 21 H 27 O 3 S) is reported, thus confirming the absolute stereochemistry of this synthetically important molecule.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"19 1","pages":"67 - 69"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84260029","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}
Thiation of N , N -biphthalimide in a search for new axially chiral ligands gave a mixture of oligothiobiphthalimides; X-ray crystallography shows that the achiral isomer of dithiodioxobiphthalimide, 1,3-dithioxo-1H-3H-[2,2 ' ]biisoindolyl-1 ' ,3 ' -dione is formed, which may imply a change in the mechanism of thiation between mono- and di-phthalimides.
N, N -联苯酰亚胺的硫代化在寻找新的轴向手性配体中得到了低硫代联苯酰亚胺的混合物;x射线晶体学表明，二硫代二氧苯酞亚胺形成了非手性异构体1,3-二硫代氧- 1h - 3h -[2,2 ']生物异吲哚-1 '，3 ' -二酮，这可能表明单邻苯酞亚胺与二邻苯酞亚胺之间的硫化机理发生了变化。
{"title":"Synthesis and X-ray structure determination of thionated biphthalimides","authors":"M. Coogan, J. Platts, R. Haigh","doi":"10.1080/02786110215844","DOIUrl":"https://doi.org/10.1080/02786110215844","url":null,"abstract":"Thiation of N , N -biphthalimide in a search for new axially chiral ligands gave a mixture of oligothiobiphthalimides; X-ray crystallography shows that the achiral isomer of dithiodioxobiphthalimide, 1,3-dithioxo-1H-3H-[2,2 ' ]biisoindolyl-1 ' ,3 ' -dione is formed, which may imply a change in the mechanism of thiation between mono- and di-phthalimides.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"37 1","pages":"251 - 257"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81501805","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}
Wet alumina supported chromium( VI) oxide performed efficient deprotection of S,S-acetals ( 1 ), 1,3-dithiolanes and 1,3-dithianes ( 2 ) under solvent-free conditions at room temperature. The reaction has been carried out in excellent yield and short reaction time under solvent-free conditions and the purification of products was straightforward.
{"title":"Deprotection of tuioacetals by wet alumina supported cr(VI) oxide under solvent-free conditions","authors":"A. Hajipour, A. Ruoho","doi":"10.1080/02786110213975","DOIUrl":"https://doi.org/10.1080/02786110213975","url":null,"abstract":"Wet alumina supported chromium( VI) oxide performed efficient deprotection of S,S-acetals ( 1 ), 1,3-dithiolanes and 1,3-dithianes ( 2 ) under solvent-free conditions at room temperature. The reaction has been carried out in excellent yield and short reaction time under solvent-free conditions and the purification of products was straightforward.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"11 1","pages":"151 - 154"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75897018","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}
Photochemical acetylthiolation of (-)-sabinene 1 afforded 10-acetylthiothujane 2 and an unexpected cyclopentenyl methyl thioacetate 3 in moderate yield (24%). Hydride reduction of these two latter compounds gave two monoterpenoid thiols ( 2a and 3a ) in excellent yield (95%). The odour of the major sulfur-containing compounds 2 and 2a was respectively described as being typically anisic and as reminiscent of cooked leek. Structural determination of these derivatives was achieved by one- and two-dimensional NMR spectroscopy.
{"title":"An unusual rearrangement of the thujane skeleton under free-radical conditions: Synthesis of thioacetates and thiols derivatives of (-)-sabinene","authors":"Karine Candela, R. Fellous, D. Joulain, R. Faure","doi":"10.1080/02786110213974","DOIUrl":"https://doi.org/10.1080/02786110213974","url":null,"abstract":"Photochemical acetylthiolation of (-)-sabinene 1 afforded 10-acetylthiothujane 2 and an unexpected cyclopentenyl methyl thioacetate 3 in moderate yield (24%). Hydride reduction of these two latter compounds gave two monoterpenoid thiols ( 2a and 3a ) in excellent yield (95%). The odour of the major sulfur-containing compounds 2 and 2a was respectively described as being typically anisic and as reminiscent of cooked leek. Structural determination of these derivatives was achieved by one- and two-dimensional NMR spectroscopy.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"168 1","pages":"145 - 149"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90135922","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}
Differently substituted 1,1-di(alkylsulfanyl)-2-nitroethylene and 2-(nitroethylene)-1,3-dithia heterocycles were synthesized and characterized on the basis of spectral data. The X-ray crystal analysis of 2-(nitromethylene)-1,3-dithietane reveals a dimeric structure, stabilized through CH-O hydrogen bonding interactions. Attempted synthesis of dithia-crown ethers from the salt did not furnish the desired products instead only 2-(nitromethylene)-1,3-dithiolane was formed in the reaction.
{"title":"Nitroketene dithioacetal chemistry: Synthesis and characterization of some 1,1-di(alkylsulfanyl)-2-nitroethylenes and 2-(nitromethylene)-1,3-dithia heterocycles","authors":"Suryanarayana Rao, L. Sakthikumar, S. Shreedevi","doi":"10.1080/02786110214497","DOIUrl":"https://doi.org/10.1080/02786110214497","url":null,"abstract":"Differently substituted 1,1-di(alkylsulfanyl)-2-nitroethylene and 2-(nitroethylene)-1,3-dithia heterocycles were synthesized and characterized on the basis of spectral data. The X-ray crystal analysis of 2-(nitromethylene)-1,3-dithietane reveals a dimeric structure, stabilized through CH-O hydrogen bonding interactions. Attempted synthesis of dithia-crown ethers from the salt did not furnish the desired products instead only 2-(nitromethylene)-1,3-dithiolane was formed in the reaction.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"14 1","pages":"207 - 218"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82037673","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}
K. Aghapoor, H. R. Darabi, K. Tabar-Heydar, L. Nakhshab
The Willgerodt-Kindler reaction of aliphatic ketones and aldehydes with sulfur and morpholine under solvent-free conditions was performed in a domestic microwave oven. The method is simple, rapid and avoids prolonged heating with solvents.
{"title":"Synthesis of aliphatic thiomorpholides by willgerodt-kindler reaction under solvent-free conditions","authors":"K. Aghapoor, H. R. Darabi, K. Tabar-Heydar, L. Nakhshab","doi":"10.1080/02786110215846","DOIUrl":"https://doi.org/10.1080/02786110215846","url":null,"abstract":"The Willgerodt-Kindler reaction of aliphatic ketones and aldehydes with sulfur and morpholine under solvent-free conditions was performed in a domestic microwave oven. The method is simple, rapid and avoids prolonged heating with solvents.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":"20 1","pages":"259 - 261"},"PeriodicalIF":0.0,"publicationDate":"2002-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75371427","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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