Pub Date : 2003-10-01DOI: 10.1080/02786110310001619978
K. M. H. Hilmy, I. El-Sayed, S. El-kousy, H. S. Slem
C-Sulfonyldithioformates 3 have been shown to be super-heterodienophiles in [4 + 2] cycloadditions with acyclic and cyclic dienes. Acyclic 1,3-dienes react with 3 in chloroform at room temperature to give the corresponding dihydrothiopyrans 4–6, while cyclopentadiene reacts with 3 to afford endo- and exo-2-thiabicyclo[2.2.1]heptene 7. Furthermore, the enophilic properties of 3 have been demonstrated by reacting 3 with tetramethylallene, 1-butene and trans-2-butene to afford the corresponding ene adducts 9, 10 and 11 respectively in quantitative yields.
c -磺酰基二硫甲酸酯3在[4 + 2]与无环和环二烯的环加成中被证明是超杂二烯亲和物。无环1,3-二烯在室温下与3在氯仿中反应得到相应的二氢噻吩4-6，环戊二烯与3反应得到内、外2-噻吩环[2.2.1]庚烯7。此外，通过与四甲基亚烯、1-丁烯和反式-2-丁烯反应，3的亲和性得到了相应的烯加合物9、10和11的定量产率。
{"title":"C-Sulfonyldithioformates as heterodienophiles and enophiles in [4 + 2] cycloaddition and ene reactions","authors":"K. M. H. Hilmy, I. El-Sayed, S. El-kousy, H. S. Slem","doi":"10.1080/02786110310001619978","DOIUrl":"https://doi.org/10.1080/02786110310001619978","url":null,"abstract":"C-Sulfonyldithioformates 3 have been shown to be super-heterodienophiles in [4 + 2] cycloadditions with acyclic and cyclic dienes. Acyclic 1,3-dienes react with 3 in chloroform at room temperature to give the corresponding dihydrothiopyrans 4–6, while cyclopentadiene reacts with 3 to afford endo- and exo-2-thiabicyclo[2.2.1]heptene 7. Furthermore, the enophilic properties of 3 have been demonstrated by reacting 3 with tetramethylallene, 1-butene and trans-2-butene to afford the corresponding ene adducts 9, 10 and 11 respectively in quantitative yields.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74646645","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 : 2003-10-01DOI: 10.1080/02786110310001619969
A. Hajipour, A. Ruoho
Various dithioacetals have been deprotected to the corresponding carbonyl compounds under solvent-free conditions using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate in the presence of aluminium chloride.
{"title":"Solid-state deprotection of dithioacetals using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate","authors":"A. Hajipour, A. Ruoho","doi":"10.1080/02786110310001619969","DOIUrl":"https://doi.org/10.1080/02786110310001619969","url":null,"abstract":"Various dithioacetals have been deprotected to the corresponding carbonyl compounds under solvent-free conditions using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate in the presence of aluminium chloride.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89005237","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 : 2003-10-01DOI: 10.1080/02786110310001622767
A. Nishimoto, Daisy Y. Zhang
The structures of thiosulfate (S2O3 2−) and four other isovalent sulfur oxyanions, S m O n 2− have been investigated at the MP2, MP4, and B3LYP levels of theory, with 6−31+G* as the basis set. By comparing the bond lengths in the dianions with those in the doubly protonated molecules, H2S m O n , the sulfur–oxygen and sulfur–sulfur bond orders have been estimated, based on a valence bond theory model. The conventional Lewis structures, which represent the central S atom as forming six covalent bonds with the four ligands, consistently give accurate descriptions of the structures for all the dianions. Natural bond order analyses, however, show that the 3d orbitals do not participate in valence bonding to any significant degree. Chemically, the peripheral sulfur atoms in all the dianions are predicted to be stronger nucleophiles as well as stronger bases than the oxygen atoms in the gas phase.
以6−31+G*为基础，在MP2、MP4和B3LYP理论水平上研究了硫代硫酸盐(S2O3 2−)和其他四个同价硫氧离子(S2O3 2−)的结构。通过比较双质子化分子(H2S m O n)和双质子化分子(H2S m O n)的键长，根据价键理论模型估计了硫氧键和硫硫键的键序。传统的路易斯结构，表示中心的S原子与四个配体形成六个共价键，一致地准确描述了所有阴离子的结构。然而，自然键序分析表明，三维轨道不参与任何程度的价键。化学上，在所有的离子中，外围的硫原子被预测为比气相中氧原子更强的亲核试剂和更强的碱。
{"title":"Hypervalency in sulfur? ab initio and DFT studies of the structures of thiosulfate and related sulfur oxyanions","authors":"A. Nishimoto, Daisy Y. Zhang","doi":"10.1080/02786110310001622767","DOIUrl":"https://doi.org/10.1080/02786110310001622767","url":null,"abstract":"The structures of thiosulfate (S2O3 2−) and four other isovalent sulfur oxyanions, S m O n 2− have been investigated at the MP2, MP4, and B3LYP levels of theory, with 6−31+G* as the basis set. By comparing the bond lengths in the dianions with those in the doubly protonated molecules, H2S m O n , the sulfur–oxygen and sulfur–sulfur bond orders have been estimated, based on a valence bond theory model. The conventional Lewis structures, which represent the central S atom as forming six covalent bonds with the four ligands, consistently give accurate descriptions of the structures for all the dianions. Natural bond order analyses, however, show that the 3d orbitals do not participate in valence bonding to any significant degree. Chemically, the peripheral sulfur atoms in all the dianions are predicted to be stronger nucleophiles as well as stronger bases than the oxygen atoms in the gas phase.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76057242","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 : 2003-10-01DOI: 10.1080/02786110310001625052
M. Chollet-Krugler, J. Burgot
3-(5-Formyl-3-thioxo-3H-[1,2]dithiol-4-yl)propionic acid has been obtained from 3-[5-(hydroxyiminomethyl)-3-thioxo-3H-[1,2]dithiol-4-yl]propionic acid under standard conditions. Conversely, for the hydroxyimino derivative the general procedure failed and so it has been prepared by the action, in a basic medium, of isoamyl nitrite on 3-(5-methyl-3-thioxo-3H-[1,2]dithiol-4-yl)propionic acid ethyl ester.
{"title":"On the preparation of 3-(5-Formyl-3-thioxo-3H-[1,2]dithiol-4-yl)-propionic acid","authors":"M. Chollet-Krugler, J. Burgot","doi":"10.1080/02786110310001625052","DOIUrl":"https://doi.org/10.1080/02786110310001625052","url":null,"abstract":"3-(5-Formyl-3-thioxo-3H-[1,2]dithiol-4-yl)propionic acid has been obtained from 3-[5-(hydroxyiminomethyl)-3-thioxo-3H-[1,2]dithiol-4-yl]propionic acid under standard conditions. Conversely, for the hydroxyimino derivative the general procedure failed and so it has been prepared by the action, in a basic medium, of isoamyl nitrite on 3-(5-methyl-3-thioxo-3H-[1,2]dithiol-4-yl)propionic acid ethyl ester.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78512812","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 : 2003-10-01DOI: 10.1080/02786110310001637617
A. Dandia, Ruby Singh, C. Mérienne, G. Morgant, A. Loupy
An improved facile one-pot synthesis of 3′-(fluorophenyl)-spiro[3H-indole-3,2′-tetrahydro-1,3-thiazine]-2,4′(1H)-dione is reported using an environmentally friendly green chemistry procedure under microwave irradiation. The crystal structure of the reported compound has been determined by a X-ray diffraction. The molecule is largely planar and has cell parameters of a = 11.181(9) Å, b = 11.06(1) Å, c = 12.715(12) Å, α = 90°, β = 98.31(7)°, γ = 90°.
报道了一种改进的微波辐射下一锅快速合成3 ' -(氟苯基)-螺[3h -吲哚-3,2 ' -四氢-1,3-噻嗪]-2,4 ' (1H)-二酮的方法。所报道的化合物的晶体结构已由x射线衍射测定。分子主要是平面,晶胞参数= 11.181 (9),b = 11.06 (1) a, c = 12.715(12),α= 90°,β= 98.31(7)°,γ= 90°。
{"title":"Solvent-free one-pot synthesis and crystal structure of a spiro[indole-thiazine]","authors":"A. Dandia, Ruby Singh, C. Mérienne, G. Morgant, A. Loupy","doi":"10.1080/02786110310001637617","DOIUrl":"https://doi.org/10.1080/02786110310001637617","url":null,"abstract":"An improved facile one-pot synthesis of 3′-(fluorophenyl)-spiro[3H-indole-3,2′-tetrahydro-1,3-thiazine]-2,4′(1H)-dione is reported using an environmentally friendly green chemistry procedure under microwave irradiation. The crystal structure of the reported compound has been determined by a X-ray diffraction. The molecule is largely planar and has cell parameters of a = 11.181(9) Å, b = 11.06(1) Å, c = 12.715(12) Å, α = 90°, β = 98.31(7)°, γ = 90°.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81263465","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 : 2003-08-01DOI: 10.1080/02786110310001593643
M. Birsa
The synthesis of 4-(2′-hydroxyaryl)-5-ethyl-2-(N,N-dialkylamino)-1,3-dithiolium salts (6a–e) has been accomplished by the heterocyclization of the corresponding carbodithioates (3a–e). The required starting materials (1a,b) have been prepared by regioselective bromination of 1-(2′-hydroxyaryl)butanones (4a,b). Under basic conditions, salts 6a–e afford anhydro-hydroxides 7a–e, which are mesoionic compounds with an intramolecular charge-transfer UV/Vis absorption where the donor moiety is linked through σ-bonded bridges (C5-S1, C4-S3) to the acceptor moiety.
{"title":"Synthesis of some 4-(2′-hydroxyaryl)-5-ethyl-2-(N, N-dialkylamino)-1,3-dithiolium salts","authors":"M. Birsa","doi":"10.1080/02786110310001593643","DOIUrl":"https://doi.org/10.1080/02786110310001593643","url":null,"abstract":"The synthesis of 4-(2′-hydroxyaryl)-5-ethyl-2-(N,N-dialkylamino)-1,3-dithiolium salts (6a–e) has been accomplished by the heterocyclization of the corresponding carbodithioates (3a–e). The required starting materials (1a,b) have been prepared by regioselective bromination of 1-(2′-hydroxyaryl)butanones (4a,b). Under basic conditions, salts 6a–e afford anhydro-hydroxides 7a–e, which are mesoionic compounds with an intramolecular charge-transfer UV/Vis absorption where the donor moiety is linked through σ-bonded bridges (C5-S1, C4-S3) to the acceptor moiety.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79997252","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 : 2003-08-01DOI: 10.1080/0278611031000138018
V. Potapov, S. Amosova, I. V. Doron'kina, R. Glass
Heating (Z)-1,2-bis(benzylseleno)ethene at 140–180 °C leads to 1,4-diselenin (79% yield) and dibenzyl selenide. This unusual reaction represents a convenient method for preparing 1,4-diselenin.
{"title":"Unexpected reaction of (Z)-1,2-bis(benzylseleno)-ethene: The formation of 1,4-diselenin","authors":"V. Potapov, S. Amosova, I. V. Doron'kina, R. Glass","doi":"10.1080/0278611031000138018","DOIUrl":"https://doi.org/10.1080/0278611031000138018","url":null,"abstract":"Heating (Z)-1,2-bis(benzylseleno)ethene at 140–180 °C leads to 1,4-diselenin (79% yield) and dibenzyl selenide. This unusual reaction represents a convenient method for preparing 1,4-diselenin.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86938238","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 : 2003-08-01DOI: 10.1080/02786110310001593643a
A. E. Ismail, A. A. El-Shehawy, A. Attia
Quinazolin-(3H)-4-thione non-nucleosides 7, 9 and 12 were obtained by the reaction of quinazolin-(3H)-4-thione 4 with compounds 5, 8 or 10 respectively. The structures of the synthesized non-nucleosides were confirmed by 1H and 13C NMR spectroscopy.
{"title":"Synthesis of N 1- and N 3-quinazolin-(3H)- 4-thione non-nucleosides","authors":"A. E. Ismail, A. A. El-Shehawy, A. Attia","doi":"10.1080/02786110310001593643a","DOIUrl":"https://doi.org/10.1080/02786110310001593643a","url":null,"abstract":"Quinazolin-(3H)-4-thione non-nucleosides 7, 9 and 12 were obtained by the reaction of quinazolin-(3H)-4-thione 4 with compounds 5, 8 or 10 respectively. The structures of the synthesized non-nucleosides were confirmed by 1H and 13C NMR spectroscopy.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75008436","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 : 2003-08-01DOI: 10.1080/02786110310001612272
G. Kong, K. Kain, I. Crandall, R. Langler
The antimalarial/anticancer (human skin cancer) properties of 11 small organosulfur compounds, some of which show antifungal and antileukemic activity, were determined using in vitro assays. Some compounds had little or no antimalarial/anticancer activity while others were highly active with IC50 values in the low µM range. Three disulfides (3, 7, 9) show encouraging activity, viz: low activity against CHO (representative mammalian) cells and significantly higher activity against human malaria (Plasmodium falciparum) cells and human skin cancer (C32) cells.
{"title":"Novel disulfides as anticancer/antimalarial agents","authors":"G. Kong, K. Kain, I. Crandall, R. Langler","doi":"10.1080/02786110310001612272","DOIUrl":"https://doi.org/10.1080/02786110310001612272","url":null,"abstract":"The antimalarial/anticancer (human skin cancer) properties of 11 small organosulfur compounds, some of which show antifungal and antileukemic activity, were determined using in vitro assays. Some compounds had little or no antimalarial/anticancer activity while others were highly active with IC50 values in the low µM range. Three disulfides (3, 7, 9) show encouraging activity, viz: low activity against CHO (representative mammalian) cells and significantly higher activity against human malaria (Plasmodium falciparum) cells and human skin cancer (C32) cells.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81532495","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 : 2003-08-01DOI: 10.1080/02786110310001612263
Christian Kaepplinger, R. Beckert, G. Braunerová, L. Zahajská, Anja Darsen, H. Goerls
The first Barton–Kellogg olefination employing thioamides or thioureas as substrates is reported. Starting from the conjugated dithioxo compounds 1 and diazocompounds 2 we substituted the C˭S groups by ester substructures mono- (type 3) and obtained the disubstituted products 4. Using the same procedure, the tricyclic thiourea 5 was converted into a new ketene aminal 6. Intermediates such as primary cycloadducts or three-membered ring-contraction products could not be isolated for any reactions studied here.
{"title":"Barton–Kellogg olefination of conjugated dithioxo compounds","authors":"Christian Kaepplinger, R. Beckert, G. Braunerová, L. Zahajská, Anja Darsen, H. Goerls","doi":"10.1080/02786110310001612263","DOIUrl":"https://doi.org/10.1080/02786110310001612263","url":null,"abstract":"The first Barton–Kellogg olefination employing thioamides or thioureas as substrates is reported. Starting from the conjugated dithioxo compounds 1 and diazocompounds 2 we substituted the C˭S groups by ester substructures mono- (type 3) and obtained the disubstituted products 4. Using the same procedure, the tricyclic thiourea 5 was converted into a new ketene aminal 6. Intermediates such as primary cycloadducts or three-membered ring-contraction products could not be isolated for any reactions studied here.","PeriodicalId":22122,"journal":{"name":"Sulfur Letters","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2003-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89638595","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}
京公网安备 11010802042870号
京ICP备2023020795号-1
扫码关注我们
求助内容：
应助结果提醒方式：