{"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}
{"title":"Radical cyclization of homopropargylic bromomethyldimethylsilyl ethers. Evidence for a hetero-trans-cycloheptene intermediate","authors":"Stéphane Bogen, Louis Fensterbank, 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}
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 , Haikang Yang , 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}
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 , Faïza Diaba , Xavier Vila , Josep Bonjoch , Elena Lago , 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}
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, Jonathan A. Kosterlitz, 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}
{"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, 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}
{"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}
{"title":"Synthesis of nitrogen heterocycles based on atom transfer carbonylation of bifunctional amines","authors":"Sergio Kreimerman , Ilhyong Ryu , Satoshi Minakata , 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}
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, Michèle Bertrand, 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}
{"title":"Approximate rate constant for the intermolecular addition of a primary alkyl radical onto bis-methanesulfonyl oxime ether","authors":"Sunggak Kim, 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}