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C-Sulfonyldithioformates as heterodienophiles and enophiles in [4 + 2] cycloaddition and ene reactions [4 + 2]环加成和烯反应中c -磺酰基二硫甲酸酯作为杂二亲烯剂和亲烯剂
Sulfur Letters Pub Date : 2003-10-01 DOI: 10.1080/02786110310001619978
K. M. H. Hilmy, I. El-Sayed, S. El-kousy, H. S. Slem
{"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}
引用次数: 1
Solid-state deprotection of dithioacetals using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate 用1-苄基-4-氮杂-1-氮杂双环[2.2.2]辛烷高碘酸盐固相脱保护二硫缩醛
Sulfur Letters Pub Date : 2003-10-01 DOI: 10.1080/02786110310001619969
A. Hajipour, A. Ruoho
{"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}
引用次数: 2
Hypervalency in sulfur? ab initio and DFT studies of the structures of thiosulfate and related sulfur oxyanions 硫的高价?硫代硫酸盐及其相关硫氧离子结构的从头算和离散傅立叶变换研究
Sulfur Letters Pub Date : 2003-10-01 DOI: 10.1080/02786110310001622767
A. Nishimoto, Daisy Y. Zhang
{"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}
引用次数: 7
On the preparation of 3-(5-Formyl-3-thioxo-3H-[1,2]dithiol-4-yl)-propionic acid 3-(5-甲酰基-3-硫氧基- 3h -[1,2]二硫醇-4-基)丙酸的制备
Sulfur Letters Pub Date : 2003-10-01 DOI: 10.1080/02786110310001625052
M. Chollet-Krugler, J. Burgot
{"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}
引用次数: 3
Solvent-free one-pot synthesis and crystal structure of a spiro[indole-thiazine] 一种螺[吲哚-噻嗪]的无溶剂一锅合成及其晶体结构
Sulfur Letters Pub Date : 2003-10-01 DOI: 10.1080/02786110310001637617
A. Dandia, Ruby Singh, C. Mérienne, G. Morgant, A. Loupy
{"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}
引用次数: 11
Synthesis of some 4-(2′-hydroxyaryl)-5-ethyl-2-(N, N-dialkylamino)-1,3-dithiolium salts 一些4-(2′-羟基)-5-乙基-2-(N, N-二烷基氨基)-1,3-二硫鎓盐的合成
Sulfur Letters Pub Date : 2003-08-01 DOI: 10.1080/02786110310001593643
M. Birsa
{"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}
引用次数: 4
Unexpected reaction of (Z)-1,2-bis(benzylseleno)-ethene: The formation of 1,4-diselenin (Z)-1,2-二(苄基硒)-乙烯的意外反应:1,4-二硒素的生成
Sulfur Letters Pub Date : 2003-08-01 DOI: 10.1080/0278611031000138018
V. Potapov, S. Amosova, I. V. Doron'kina, R. Glass
{"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}
引用次数: 5
Synthesis of N 1- and N 3-quinazolin-(3H)- 4-thione non-nucleosides 1-和3-喹唑啉-(3H)- 4-硫酮非核苷的合成
Sulfur Letters Pub Date : 2003-08-01 DOI: 10.1080/02786110310001593643a
A. E. Ismail, A. A. El-Shehawy, A. Attia
{"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}
引用次数: 3
Novel disulfides as anticancer/antimalarial agents 新型二硫化物作为抗癌/抗疟剂
Sulfur Letters Pub Date : 2003-08-01 DOI: 10.1080/02786110310001612272
G. Kong, K. Kain, I. Crandall, R. Langler
{"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}
引用次数: 17
Barton–Kellogg olefination of conjugated dithioxo compounds 共轭二硫氧化合物的巴顿-凯洛格烯化反应
Sulfur Letters Pub Date : 2003-08-01 DOI: 10.1080/02786110310001612263
Christian Kaepplinger, R. Beckert, G. Braunerová, L. Zahajská, Anja Darsen, H. Goerls
{"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}
引用次数: 7
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