Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry最新文献

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Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01273-7
Samir Z Zard, Samir Z Zard
{"title":"Avant-propos","authors":"Samir Z Zard, Samir Z Zard","doi":"10.1016/S1387-1609(01)01273-7","DOIUrl":"https://doi.org/10.1016/S1387-1609(01)01273-7","url":null,"abstract":"","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Page 389"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01273-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138259199","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: 0
Radical cyclization of homopropargylic bromomethyldimethylsilyl ethers. Evidence for a hetero-trans-cycloheptene intermediate 同丙基溴甲基二甲基硅基醚的自由基环化。杂反式环庚烯中间体的证据
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01247-6
Stéphane Bogen, Louis Fensterbank, Max Malacria
{"title":"Radical cyclization of homopropargylic bromomethyldimethylsilyl ethers. Evidence for a hetero-trans-cycloheptene intermediate","authors":"Stéphane Bogen,&nbsp;Louis Fensterbank,&nbsp;Max Malacria","doi":"10.1016/S1387-1609(01)01247-6","DOIUrl":"10.1016/S1387-1609(01)01247-6","url":null,"abstract":"<div><p>This communication describes our preliminary results on the radical cyclization of homopropargylic bromomethyldimethylsilyl ethers, an unknown reaction. With precursor <strong>5a</strong>, only the very rare 7-<em>endo</em>-<em>dig</em> process was observed. The reduction of the resulting vinyl radical is not stereoselective and gives a <em>cis</em>/<em>trans</em>, 1.35:1 mixture of silaoxepan derivatives, as determined after a methyllithium treatment yielding olefins <strong>11</strong> and <strong>12</strong>. This represents a new example of formation of a <em>trans</em> heterocyclic cycloheptene. With disubstituted precursor <strong>5b</strong>, the system is less reactive and still no 6-<em>exo</em>-<em>dig</em> radical cyclization has been observed.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 423-426"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01247-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79701587","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: 0
Synthesis and in vitro activity of a non-epimerizable analog of the angiotensin-converting enzyme inhibitor A58365A 血管紧张素转换酶抑制剂A58365A不可外渗类似物的合成及体外活性研究
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01263-4
Derrick L.J Clive , Haikang Yang , Richard Z Lewanczuk
{"title":"Synthesis and in vitro activity of a non-epimerizable analog of the angiotensin-converting enzyme inhibitor A58365A","authors":"Derrick L.J Clive ,&nbsp;Haikang Yang ,&nbsp;Richard Z Lewanczuk","doi":"10.1016/S1387-1609(01)01263-4","DOIUrl":"10.1016/S1387-1609(01)01263-4","url":null,"abstract":"<div><p>The 3-methyl-substituted analog (±)-<strong>3</strong> of the angiotensin converting enzyme inhibitor A58365A (<strong>1</strong>) was synthesized from lactone <strong>4</strong> and amino acid ester <strong>16</strong>, via key intermediates <strong>18</strong>, <strong>19</strong> and <strong>21a</strong>,<strong>b</strong>. Compound (±)-<strong>3</strong> was found to possess powerful ACE inhibitory activity (<em>IC</em><sub>50</sub> = ca 500 nM), as judged by in vitro tests against porcine kidney ACE, under conditions in which the commercial drug captopril has <em>IC</em><sub>50</sub> = 280 nM.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 505-512"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01263-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76853297","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
An unexpected course in the 6-exo radical cyclizations of trichloroacetamides on changing the N-substituent from benzyl to α-methylbenzyl 三氯乙酰胺6-外显基环化反应中n取代基由苄基变为α-甲基苄基的意外过程
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01261-0
Josefina Quirante , Faïza Diaba , Xavier Vila , Josep Bonjoch , Elena Lago , Elies Molins
{"title":"An unexpected course in the 6-exo radical cyclizations of trichloroacetamides on changing the N-substituent from benzyl to α-methylbenzyl","authors":"Josefina Quirante ,&nbsp;Faïza Diaba ,&nbsp;Xavier Vila ,&nbsp;Josep Bonjoch ,&nbsp;Elena Lago ,&nbsp;Elies Molins","doi":"10.1016/S1387-1609(01)01261-0","DOIUrl":"10.1016/S1387-1609(01)01261-0","url":null,"abstract":"<div><p>Radical cyclization of <em>N</em>-(α-methyl)benzyl substituted trichloroacetamides upon α,β-unsaturated nitriles has been studied. Tributyltin hydride treatment of trichloroacetamides <strong>5a</strong> and <strong>5b</strong> gives morphan derivatives (<strong>1</strong> and <strong>2</strong>), through a 6-<em>exo</em>-trig radical cyclization, and unexpectedly normorphans <strong>6</strong> and <strong>7</strong> as a result of a stereoespecific process in which the stereogenic benzylic carbon undergoes a configurational inversion.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 513-521"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01261-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74485952","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
Tandem radical addition reactions to substituted indoles under atom-transfer and oxidative conditions 原子转移和氧化条件下取代吲哚的串联自由基加成反应
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01252-X
Jeffrey H. Byers, Jonathan A. Kosterlitz, Peter L. Steinberg
{"title":"Tandem radical addition reactions to substituted indoles under atom-transfer and oxidative conditions","authors":"Jeffrey H. Byers,&nbsp;Jonathan A. Kosterlitz,&nbsp;Peter L. Steinberg","doi":"10.1016/S1387-1609(01)01252-X","DOIUrl":"10.1016/S1387-1609(01)01252-X","url":null,"abstract":"<div><p>The dimethyl methylmalonyl radical was generated upon photolysis of dimethyl bromomethylmalonate or treatment of dimethyl methylmalonate with Mn(OAc)<sub>3</sub>·2 H<sub>2</sub>O. This radical was added to an exocyclic olefin appended to 1-acyl or 3-acyl indoles, with subsequent cyclization to generate 1,2- or 2,3- fused indole derivatives, respectively.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 471-476"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01252-X","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77907091","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
Tributyltin hydride-mediated free radical cyclization of allene-tethered oxime ethers, oxime esters and hydrazones. Influence of the substituents borne by the C=N double bond on the course of the reaction 三丁基锡氢化介导的烯系肟醚、肟酯和腙自由基环化。C=N双键所载取代基对反应过程的影响
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01264-6
Michaël Depature, Jacques Hatem
{"title":"Tributyltin hydride-mediated free radical cyclization of allene-tethered oxime ethers, oxime esters and hydrazones. Influence of the substituents borne by the C=N double bond on the course of the reaction","authors":"Michaël Depature,&nbsp;Jacques Hatem","doi":"10.1016/S1387-1609(01)01264-6","DOIUrl":"10.1016/S1387-1609(01)01264-6","url":null,"abstract":"<div><p>A set of allenic derivatives <strong>1</strong> bearing a C=N bond in β position and diversely substituted in R<sup>3</sup> and Z was prepared. The behaviour of compounds <strong>1</strong> towards the Bu<sub>3</sub>Sn<sup>•</sup> radical was then studied. Depending on the nature of R<sup>3</sup> and Z, products <strong>2</strong>, <strong>3</strong>, and <strong>4</strong> were obtained in diverse ratios. When the steric hindrance on the C-atom of the C=N bond was low (R<sup>3</sup> = H), the product ‘normally’ obtained was <strong>2</strong>. When the steric hindrance of R<sup>3</sup> was higher, the formation of <strong>3</strong> and <strong>4</strong> became competitive. In this case, the ratio between <strong>2</strong>, <strong>3</strong>, and <strong>4</strong> can be explained on the basis of the polarity of R<sup>3</sup> and Z. The higher the electroattractive effect of R<sup>3</sup> and Z, the higher the quantity of <strong>2</strong> and <strong>4</strong> in comparison with <strong>3</strong>.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 523-529"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01264-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77291021","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: 0
Free radical cyclisation of enamides leading to biologically important γ-lactams 自由基环化导致重要的生物γ-内酰胺
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01255-5
Andrew F Parsons
{"title":"Free radical cyclisation of enamides leading to biologically important γ-lactams","authors":"Andrew F Parsons","doi":"10.1016/S1387-1609(01)01255-5","DOIUrl":"10.1016/S1387-1609(01)01255-5","url":null,"abstract":"<div><p>This review describes the free radical cyclisation of enamides using tributyltin hydride, manganese(III) acetate, copper(I) complexes or dichlorotris(triphenylphosphine)ruthenium(II). These cyclisations can proceed via either 4-<em>exo</em> or 5-<em>endo</em> pathways, to produce β- or γ-lactam products, respectively. In general, the reactions produce γ-lactams derived from an unusual (disfavoured) 5-<em>endo</em>-<em>trig</em> radical cyclisation. These results can be explained on the basis of a reversible cyclisation mechanism; the 4-<em>exo</em> cyclisation produces the kinetically favoured β-lactam while the 5-<em>endo</em> cyclisation produces the thermodynamically more stable γ-lactam.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 391-400"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01255-5","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80553802","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
Synthesis of nitrogen heterocycles based on atom transfer carbonylation of bifunctional amines 基于双功能胺原子转移羰化的氮杂环合成
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01253-1
Sergio Kreimerman , Ilhyong Ryu , Satoshi Minakata , Mitsuo Komatsu
{"title":"Synthesis of nitrogen heterocycles based on atom transfer carbonylation of bifunctional amines","authors":"Sergio Kreimerman ,&nbsp;Ilhyong Ryu ,&nbsp;Satoshi Minakata ,&nbsp;Mitsuo Komatsu","doi":"10.1016/S1387-1609(01)01253-1","DOIUrl":"10.1016/S1387-1609(01)01253-1","url":null,"abstract":"<div><p>Combining atom transfer carbonylations of bifunctional amines with an appropriate choice of cyclization conditions enables the preparation of nitrogen-containing heterocycles via the incorporation of carbon monoxide.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 497-503"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01253-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83351800","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
Stereoinduction in the tosyl radical-mediated cyclization of polysubstituted 1,6-dienes derived from d-glucose and d-mannose 从d-葡萄糖和d-甘露糖衍生的多取代1,6-二烯的tosyl自由基介导环化的立体诱导
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01251-8
Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier
{"title":"Stereoinduction in the tosyl radical-mediated cyclization of polysubstituted 1,6-dienes derived from d-glucose and d-mannose","authors":"Dora-Marina Gutierrez-Avella,&nbsp;Michèle Bertrand,&nbsp;Robert Nouguier","doi":"10.1016/S1387-1609(01)01251-8","DOIUrl":"10.1016/S1387-1609(01)01251-8","url":null,"abstract":"<div><p>Polysubstituted 1,6-dienes <strong>1</strong> and <strong>6</strong>, derived from 6-iodo-<span>d</span>-manno- and <span>d</span>-glucopyranosides through Boord fragmentation and subsequent olefination, undergo cyclization upon addition of TsSePh under radical conditions. Functionalized cyclopentitols result from tributyltin hydride mediated reduction of the adducts. A tentative rationalization of steroinduction is given, and a comparison is made with related data in the literature.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 453-459"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01251-8","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78809869","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: 0
Approximate rate constant for the intermolecular addition of a primary alkyl radical onto bis-methanesulfonyl oxime ether 伯烷基自由基在双甲磺酰肟醚分子间加成的近似速率常数
Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry Pub Date : 2001-06-01 DOI: 10.1016/S1387-1609(01)01258-0
Sunggak Kim, Yukwan Song
{"title":"Approximate rate constant for the intermolecular addition of a primary alkyl radical onto bis-methanesulfonyl oxime ether","authors":"Sunggak Kim,&nbsp;Yukwan Song","doi":"10.1016/S1387-1609(01)01258-0","DOIUrl":"10.1016/S1387-1609(01)01258-0","url":null,"abstract":"<div><p>An approximate rate constant for the intermolecular addition of a primary alkyl radical onto bis-methanesulfonyl oxime ether <strong>2</strong> has been measured to be <em>k</em><sub>a</sub> = 1.7·10<sup>6</sup> M<sup>–1</sup>·s<sup>–1</sup> at 80 <sup>o</sup>C, which is in reasonably good agreement with the data obtained from competition experiments.</p></div>","PeriodicalId":100305,"journal":{"name":"Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry","volume":"4 6","pages":"Pages 431-433"},"PeriodicalIF":0.0,"publicationDate":"2001-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1387-1609(01)01258-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74444062","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: 0
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