Graphical Abstracts
2005; Taylor & Francis; Volume: 35; Issue: 12 Linguagem: Inglês
10.1081/scc-200065674
ISSN1532-2432
ResumoAbstract Synth. Commun. 2005, 35, 1567 USE OF OLIGOSALICYLATES IN THE PREPARATION OF PHENOLIC AMIDO ACIDS David Gschneidner, JoAnne Corvino, John Freeman, Doris O'Toole, Lynn Shields, and Eric Wang Emisphere Technologies Inc., Tarrytown, New York, USA A simplified methodology has been developed for preparing salicylamides from the corresponding acids via oligosalicylates, which protect the phenolic group while at the same time activating the carboxyl for coupling. Synth. Commun. 2005, 35, 1577 VANADYL TRIFLATE AS AN EFFICIENT AND RECYCLABLE CATALYST FOR THE SYNTHESIS OF α‐AMINONITRILES Surya Kanta De Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy, Purdue Cancer Center, Purdue University, West Lafayette, Indiana, USA Synth. Commun. 2005, 35, 1583 IMPROVED SYNTHESIS OF C 2‐SYMMETRIC 4,4′‐α,ω‐ALKYLENEDIOXY‐BIS‐(3‐METHOXYBENZALDEHYDES) Pepe' S. Maley, Rachel M. Anderson, and David E. Lewis Department of Chemistry, University of Wisconsin—Eau Claire, Eau Claire, Wisconsin, USA An improved Williamson synthesis of C 2‐symmetric 4,4′‐(α,ω‐alkylenedioxy)‐bis(3‐methoxy‐benzaldehydes) from vanillin is described. Synth. Commun. 2005, 35, 1589 SELECTIVE REDUCTIONS OF C‐(4,6‐O‐BENZYLIDENE‐β‐D‐GLUCOPYRANOSYL) NITROMETHANE Ondrej Simo,1 Katja Michael,2 Wesley Yoshida,2 Vyacheslav A. Chertkov,1 and Paul H. Gross1 1Department of Chemistry, University of the Pacific, Stockton, California, USA 2Department of Chemistry, University of Hawaii, Honolulu, Hawaii, USA Synth. Commun. 2005, 35, 1601 GENERALIZED METHOD FOR THE PRODUCTION OF 1,3‐BENZOXAZINE, 1,3‐BENZOTHIAZINE, AND QUINAZOLINE DERIVATIVES FROM 2‐(HYDROXY, THIO, OR AMINO) AROMATIC ACIDS USING TRIPHENYLPHOSPHINE THIOCYANOGEN Kaylene M. Pritchard,1 Jasim M. Al‐Rawi,1 and Andrew B. Hughes2 1School of Pharmacy and Applied Science, La Trobe University, Bendigo, Australia 2Department of Chemistry, La Trobe University, Victoria, Australia Synth. Commun. 2005, 35, 1613 APPLICATION OF THE PMC PROTECTING GROUP IN THE EFFICIENT SYNTHESIS OF 4,4‐DISUBSTITUTED PIPERIDINES Janet L. Ralbovsky, Joseph G. Lisko, and Wei He Drug Discovery, Johnson & Johnson Pharmaceutical Research and Development, LLC, Welsh and McKean Roads, P.O. Box 776, Spring House, PA 19477, USA An efficient synthesis of the 4,4‐disubstituted piperidine scaffold 1 was accomplished by treating the PMC N‐protected α,β‐unsaturated ethyl cyanoacetate 9 with various Grignard reagents (R1MgX). Subsequent heating at 190°C in a strong base provided carboxylic acids 12–20b in good yield. The PMC group was easily removed at room temperature with 33% HBr in acetic acid. Synth. Commun. 2005, 35, 1627 GREEN ALKOXYIODINATION OF CYCLOHEXENE MEDIATED BY NATURAL CLAY Raul A. S. Villegas,1 José Luiz do Espírito Santo Jr.,2 Antonio M. Sanseverino,1 Marcio C. S. de Mattos,1 Mônica R. M. P. de Aguiar,2 and Alcides W. S. Guarino3 1Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, Caixa Postal 68545, CEP 21945‐970, Rio de Janeiro, Brazil 2Departamento de Química Orgânica, Instituto de Química, Universidade do Estado do Rio de Janeiro, CEP 20550‐013 Rio de Janeiro, Brazil 3Departamento de Ciências Naturais, Escola de Ciências Biológicas, Universidade Federal do Estado do Rio de Janeiro, Rio de Janeiro, Brazil Synth. Commun. 2005, 35, 1633 NAZAROV APPROACH TO 4‐BENZOYLOXYMETHYL‐CYCLOPENT‐2‐ENONE, A PRECURSOR TO THE HELMINTHOSPOROLS Justin K. Belardi, Lindsay A. Curtis, Steven S. Clareen, Heidi L. Shimp, Catherine E. Leimkuhler, Nicole L. Simonowicz, and Eduard Casillas Department of Chemistry, Villanova University, Villanova, Pennsylvania, USA A short, scalable route to 4‐hydroxymethylcyclopent‐2‐enone, based upon a silicon‐directed Nazarov cyclization, is described. Noteworthy in this study is the success of the cyclization with an oxygenated substrate. Synth. Commun. 2005, 35, 1641 CONVENIENT SYNTHESIS OF SUBSTITUTED 5‐(HYDROXYMETHYL)‐8‐METHYL‐3‐(4‐PHENYLQUINAZOLIN‐2‐YL)‐2H‐PYRANO[2,3‐C]PYRIDIN‐2‐ONES Irina O. Zhuravel,1 Sergiy M. Kovalenko,2 Alexandre V. Ivachtchenko,3 Valentin P. Chernykh,1 and Pavlo E. Shinkarenko 1National Pharmaceutical University, Kharkiv, Ukraine 2Institute of Combinatorial Organic Chemistry, Kharkiv, Ukraine 3ChemDiv, Inc., San Diego, USA Synth. Commun. 2005, 35, 1649 PREPARATION OF CI‐1027 GLUCURONIDE: METABOLITE OF A REMARKABLE LIPID‐MODULATING AGENT A. Akin and T. T. Curran Pfizer Global Research and Development, Pharmaceutical Sciences, Ann Arbor, MI, USA The preparation of the 1β‐glucuronide of the diacid, CI‐1027 is described. Synth. Commun. 2005, 35, 1663 EXPEDITIOUS METHOD FOR SYNTHESIS OF SYMMETRICAL 1,3‐DISUBSTITUTED UREAS AND THIOUREAS Shahnaz Perveen,1 Syed Muhammad Abdul Hai,1 Rashid Ali Khan,1 Khalid Mohammed Khan,2 Nighat Afza,1 and Tahira B. Sarfaraz1 1PCSIR Laboratories Complex Karachi, Off University Road, Karachi, Pakistan 2H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi, Pakistan 1,3‐Disubstituted ureas and thioureas are synthesized from isocyanates, düsocyanates, and thioisocyanates, respectively, in the presence of tertiary amines at room temperature in high yields. Synth. Commun. 2005, 35, 1675 ASYMMETRIC SYNTHESIS OF ω‐BROMO‐2(S)‐METHYL ACIDS AS PRECURSORS FOR NOVEL ARGININE, LYSINE, AND MERCAPTO RESIDUES M. Kyle Hadden,1 Kyle P. Kokko,1 and Thomas A. Dix1,2 1Department of Pharmaceutical Sciences, Medical University of South Carolina, Charleston, South Carolina, USA 2Argolyn Biosciences Inc., Mt. Pleasant, South Carolina, 29464, USA Synth. Commun. 2005, 35, 1681 ORGANIC REACTIONS IN WATER: SYNTHESIS OF PHENACYL ESTERS FROM PHENACYL BROMIDE AND POTASSIUM SALTS OF AROMATIC ACIDS IN THE PRESENCE OF β‐CYCLODEXTRIN M. Narender, M. Somi Reddy, V. Pavan Kumar, and K. Rama Rao Organic Chemistry Division‐I, Indian Institute of Chemical Technology, Hyderabad‐500 007, India Synth. Commun. 2005, 35, 1687 SYNTHETIC APPROACHES TO SPOROCHNOLS A–C A. Srikrishna, G. Satyanarayana, and M. R. Prasad Department of Organic Chemistry, Indian Institute of Science, Bangalore, India Synth. Commun. 2005, 35, 1699 SYNERGISM OF MICROWAVES AND IMMOBILIZED ENZYME CATALYSIS IN SYNTHESIS OF ADIPIC ACID ESTERS IN NONAQUEOUS MEDIA Ganapati D. Yadav and Piyush S. Lathi Department of Chemical Engineering, University Institute of Chemical Technology (UICT), University of Mumbai, Matunga, Mumbai, India Synth. Commun. 2005, 35, 1707 EtOH/Ba(OH)2 TRIGGERS SELF‐CONDENSATION OF (E)‐1,4‐DIARYL‐2‐BUTENE‐1,4‐DIONES TO CYCLOPENTANOL DERIVATIVES H. Surya Prakash Rao and S. P. Senthilkumar Department of Chemistry, Pondicherry University, Pondicherry, India Synth. Commun. 2005, 35, 1715 NOVEL ONE‐POT SYNTHESIS OF ACETOXY‐2,4‐CYCLOHEXADIENONES Pradeep T. Deota,1 Piyush R. Upadhyay,2 and Hemant S. Parmar1 1Applied Chemistry Department, Faculty of Technology and Engineering, The Maharaja Sayajirao University of Baroda, Vadodara, India 2Department of Chemistry, Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara, India Synth. Commun. 2005, 35, 1725 ASYMMETRIC ALLYLATION OF ALDIMINES WITH INDIUM AND (+)‐CINCHONINE Rongbi Han,1,2 Seung Hyuk Choi,1 Kee In Son,1 Young Moo Jun,1 Byung Min Lee,3 and Byeong Hyo Kim1 1Department of Chemistry, Kwangwoon University, Seoul, South Korea 2Department of Chemistry, Yanbian University, Jilin, China 3KRICT, Taejon, South Korea By applying indium and allyl bromide, aldimines were converted into homoallyl amines with excellent yields. The presence of (+)‐cinchonine to the reaction mixture yielded enantioselective allylation with 22–44%ee.
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