The Open Organic Chemistry Journal最新文献

{"title":"An Efficient and Concise Synthesis of Heteroaryldipyrromethanes, Tetrapyrazolylporphyrins and Metalloporphyrins","authors":"Farhanullah, V. Ram","doi":"10.2174/1874095200903010042","DOIUrl":"https://doi.org/10.2174/1874095200903010042","url":null,"abstract":"One pot synthesis of terpyrromethanes (3a) and (di(1H-pyrrol-2-yl)methyl)heteroarenes (3b-m) has been de- lineated by Amberlyst 15 catalyzed condensation of pyrrole and heterocyclic aldehydes (2), not reported earlier. The com- pounds 3a and 3b have been formylated to 5-(di(5-formyl-1H-pyrrol-2-yl)methyl)-1H-pyrrole-2-carbaldehyde (4a) and 5- ((5-formyl-1H-pyrrol-2-yl)(3-pyridinyl)methyl)-1H-pyrrole-2-carbaldehyde (4b), by using a mixture of POCl 3 and DMF as formylating agent. Similarly, 5-alkyl-1H-pyrrole-2-carbaldehyde (8) has also been prepared from 2-alkyl-1H-pyrroles (6), obtainable by acylation followed by Wolf-Kishner reduction. Amberlyst 15 / TFA catalyzed the condensation of 8 with pyrrole which gave 3a instead of expected product 10, due to an unusual cleavage of alkyl substituent at position 5 in 8. CS 2 addition to 6 followed by methylation provided methyl 5-alkyl-1H-pyrrole-2-carbodithioates (7), which on reaction with hydrazine hydrate yielded 5-alkyl-1H-pyrrole-2-carbothiohydrazide (9). Tetrapyrazolylporphyrins (12) have been synthesized directly by condensation of pyrrole with 3-aryl-4-formyl-1-phenylpyrazole (11) in propionic acid. These por- phyrins were transformed to metalloporphyrins (13) from reaction with zinc and copper acetate separately.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"38 1 1","pages":"42-48"},"PeriodicalIF":0.0,"publicationDate":"2009-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89140997","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":"Smiles Rearrangement in the Synthesis of Di- and Triiodinated 5- (Acylamino)-1,3-Benzenedicarboxamides","authors":"P. Anelli, M. Brocchetta, E. Cappelletti, V. Vincenzi","doi":"10.2174/1874095200903010035","DOIUrl":"https://doi.org/10.2174/1874095200903010035","url":null,"abstract":"Both the number and the position of iodine atoms on the aromatic ring of polyiodinated N,N'-bis(2,3- dihydroxypropyl)-5-(2-methylamino-2-oxoethoxy)-1,3-benzenedicarboxamides are crucial to define the structure of the product obtained by treatment with aqueous NaOH. The 2,6-diiodo and the 2,4,6-triiodo derivatives give the correspond- ing Smiles rearrangement products in 77 and 96% yields, respectively. Conversely, under the same conditions, the 2,4- diiodo isomer predominantly undergoes hydrolysis of the phenoxyacetamide moiety.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"9 1","pages":"35-41"},"PeriodicalIF":0.0,"publicationDate":"2009-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79608936","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 Pyrene-Anthracene Conjugated Molecular Rods","authors":"J. Chávez, S. Ortega, M. Martínez-García","doi":"10.2174/1874095200903010011","DOIUrl":"https://doi.org/10.2174/1874095200903010011","url":null,"abstract":"Fully conjugated pyrene-anthracene-based molecular rods were synthesized by the Horner-Wadsworth- Emmons reaction utilizing potassium tert-butoxide in dry THF. The synthesized rods, which have butylene groups as solubility spacers in the main chain, exhibited good solubility in polar solvents. The solutions of the synthesized pyrene- containing molecular rods exhibited a blue shift in the UV-vis from the absorption maximum due to the presence of the pyrene group in comparison with the dialdehydes. The chemical structure and purity of the synthesized rods were con- firmed by 1 H and 13 C NMR, FAB+, MALDI-TOF, electrospray mass spectra and elemental analysis. The presence of charge-transfer reaction centers in mac- romolecules depends on factors as the composition, the sepa- ration in the interchromophore, the overall dynamical and supramolecular reorganization, and the electronic coupling (1). The synthesis of artificial charge-transfer model systems in which the introduction of simple molecular changes is used to control and tune the magnitude of the electron- transfer parameters became a theme of great interest in the last years. The molecular chains or bridges inside the mole- cule provide endless opportunities, since they determine the structural features and the size of the electronic coupling between the donor and acceptor fragments (2). The modifica- tion of the spacer gives the possibility to introduce a system- atic alteration of separation, orientation, and overlap without affecting the electronic nature of the donor-acceptor pair, for which the coupling is proportional to the overlap of their electronic clouds (3). The electron-transfer processes depend on molecular size and structure, as well as the temperature and the free-energy difference between the donor and accep- tor in donor-bridge-acceptor systems. Currently, monodis- perse and soluble  -conjugated systems with a well-defined length and composition are receiving a growing interest for the design of molecular wires (4) and rods (5), since they can be used as tunable building blocks (6) for nanoscale chemi-","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"15 1","pages":"11-21"},"PeriodicalIF":0.0,"publicationDate":"2009-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87915718","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 3- Benzylidene, 5-Substituted 3-Benzylidene, 3- Hetarylmethylene and 5-Substituted Hetarylmethylene Derivatives of Indolin- 2-ones","authors":"Haribabu Ankati, S. K. Akubathini, S. Kamila, Chandrani Mukherjee, S. D’Mello, E. Biehl","doi":"10.2174/1874095200903010001","DOIUrl":"https://doi.org/10.2174/1874095200903010001","url":null,"abstract":"A wide variety of titled compounds, several of which have neuro-protecting properties has been prepared in yields ranging between 70 to 90%. The compounds were identified by 1 HNMR, 13 C NMR, 1D and 2D NOE analysis, and HRMS. An investigation of the effect of certain 5-substitutuents on the E to Z ratios in DMSO-d6 was carried out. The 5- nitro and 5-acetyl substituents were not isomerized, whereas the 5-fluoro, 5-chloro and 5-bromo underwent significant isomerization. In the former cases resonance interaction of the lone pair electrons of NH group of the indolin-2-one with the 5-nitro or 5-acetyl of the indolin-2-one prevents rotation of the benzylidene C=C bond whereas in the case of the latter 5-halo substituent, the lone pair electrons on the NH group interacts with the benzylidene C=C bond giving rise to anionic C-C - bond in which rotation about this bond can occur.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"35 1","pages":"1-10"},"PeriodicalIF":0.0,"publicationDate":"2009-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82181505","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":"Solid State and Solution Structure of an Unusual Compound Containing a CS7 Ring~!2008-04-06~!2008-11-16~!2008-12-03~!","authors":"H. Offermanns, J. Martens, Martin Watzke, P. Albers, B. Hannebauer, M. Janik, A. Müller, K. Shankland, Charlotte K. Leech, S. Parker","doi":"10.2174/1874095200802010110","DOIUrl":"https://doi.org/10.2174/1874095200802010110","url":null,"abstract":"","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"125 1","pages":"110-113"},"PeriodicalIF":0.0,"publicationDate":"2008-12-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76678277","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":"The First Synthesis of p-Cl- and p-F-Phenylverbenene","authors":"Claudia A Contreras-Celedón, L. Chacón-García","doi":"10.2174/1874095200801020100","DOIUrl":"https://doi.org/10.2174/1874095200801020100","url":null,"abstract":"The first synthesis of 4´-X-phenylverbenene (X = F and Cl) via reaction of myrtenal with 4� -X phenylmagne- sium bromide and Bi(NO3)3 is described. Verbenene is formed due to the electron-withdrawing effect of the 4� - electronegative group, either fluorine or a Cl-Bi complex.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"27 1","pages":"100-106"},"PeriodicalIF":0.0,"publicationDate":"2008-11-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82832991","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":"Solvent-Free Synthesis of Fused Pyrazolo[1,5-a]pyrimidines by Reaction of 5-Amino-1H-pyrazoles and β -Triketones","authors":"J. Quiroga, J. Portilla, Silvia Cruz, R. Abonía, B. Insuasty, M. Nogueras, J. Cobo, M. Hursthouse","doi":"10.2174/1874095200801020092","DOIUrl":"https://doi.org/10.2174/1874095200801020092","url":null,"abstract":"The solvent-free reaction between 5-amino-1H-pyrazoles and  -triketones (2-acetyldimedone and 2- acetylindandione) leads to the formation of new fused pyrazolo(1,5-a)pyrimidines in good yields. A possible mechanistic route is postulated on the basis of the isolation of the cyclization intermediate. The structures and regiospecificity of the reaction were determined on the basis of nmr measurements and X-ray diffraction.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"65 1","pages":"92-99"},"PeriodicalIF":0.0,"publicationDate":"2008-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74420646","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":"Chromone-3-carboxaldehydes in Passerini Reactions Using TosMIC as the Isonitrile Component","authors":"Michael A. Terzidis, J. Stephanidou-Stephanatou, C. Tsoleridis","doi":"10.2174/1874095200801020088","DOIUrl":"https://doi.org/10.2174/1874095200801020088","url":null,"abstract":"p-Toluenesulfonylmethyl isocyanide (TosMIC) is used as the isonitrile component in Passerini reactions with chromone-3-carboxaldehydes to yield chromenyl-amidoesters in good yields.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"168 1","pages":"88-91"},"PeriodicalIF":0.0,"publicationDate":"2008-08-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77775324","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":"A Convenient Method for the Synthesis of 1,5-benzodiazepin-2-one","authors":"M. Rida, H. E. Meslouhi, N. H. Ahabchane, B. Garrigues, N. Es‐Safi, E. Essassi","doi":"10.2174/1874095200801020083","DOIUrl":"https://doi.org/10.2174/1874095200801020083","url":null,"abstract":"New 3-hydroxy-1,5-benzodiazepin-2-ones were synthesized through condensation between o- phenylenediamines with glycidic ester. Alkylation and oxidation of some of the obtained compounds were also explored in different conditions yielding various oxidized and alkylated benzodiazepines. The structural elucidation of the synthe- sized compounds was achieved by MS, NMR spectroscopy and also through X-ray diffraction analysis. The glycidic ester was thus shown to be an interesting synthon in the synthesis of new 1,5-benzodiazepines used in alkylation and oxidation reactions. Synthesis of 3-hydroxy -4-phenyl tetrahydro-1,5- benzodiazepin-2-one (4) and (5) A mixture of o-phenylenediamine 1 or its dimethylated derivative 2 (0.03 mole) and ethyl glycidate (0.03 mole) was refluxed in 80 mL of xylene during 48 hours. The obtained crude mixture was left at room temperature during one night. The trans diastereoisomers 4a or 5a which precipitate were filtered under reduced pressure.","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"39 1","pages":"83-87"},"PeriodicalIF":0.0,"publicationDate":"2008-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90564995","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":"Suzuki - Miyaura Reaction of 4-Silyl-bromobenzenes with Phenylboronic Acid under Thermal and Microwave Conditions~!2008-03-27~!2008-05-15~!2008-06-10~!","authors":"I. Greiner, E. Hohmann, L. Vida, G. Keglevich","doi":"10.2174/1874095200802010065","DOIUrl":"https://doi.org/10.2174/1874095200802010065","url":null,"abstract":"","PeriodicalId":23020,"journal":{"name":"The Open Organic Chemistry Journal","volume":"71 1 1","pages":"65-67"},"PeriodicalIF":0.0,"publicationDate":"2008-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82284274","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}