Organic Preparations and Procedures International
The New Journal for Organic Synthesis


Table of Contents Volume 27, 1995



Synthesis and Chemistry of Melatonin and of Related Compounds. A Review by H. M. Hugel* and D. J. Kennaway1
Trifluoromethyl and Perfluoroalkyl Derivatives of Azoles. A Review by J. Elguero*, A. Fruchier, N. Jagerovic and A. Werner33
Synthesis of Halogenated Isoxazolyl Naphthoquinones by V. G. Dabbene, M. C. Briñón* and M. M. de Bertorello75
OPPI Briefs (J.-P. Anselme, Editor)81
Efficient Reduction of Nitroarenes to Amines by Sodium Borohydride and Cuprous Bromide-Dimethyl Sulfide by H. V. Patel*, K. A. Vyas, S. P. Pandey and P. S. Fernandes81
Iodination of Naphthoquinones and Coumarin catalyzed by Ceric Ammonium and Mercuric Nitrates by J. Sharma, P. K. Singh, K. P. Singh and R. N. Khanna*84
The Synthesis and Characterization of Novel bis(Formazans) by Y. Gok* and H. B. Senturk87
Inverse-Electron Demand Diels-Alder Cyclocondensations in the Synthesis of 5-8-5 Fused Ring Systems by J. G. Garcia* and M. L. McLaughlin92
Transformation of Carboxylic Esters to Aldehydes with Sodium tris(Diethylamino)-aluminum Hydride by J. S. Cha*, J. M. Kim, M. K. Jeoung, O. O. Kwon, and E. J. Kim95
Synthesis of Allyl Ethenyl Ethers Using S-Ethylsulfilmines by T. Yamamoto*, S. Fujita, K. Sugawara and T. Watanabe99
Synthesis of 2-Substituted 3,4-Dihydrooxazoles Using S-Ethenylsulfilimines by K. Ikeda, H. Honda, T. Matsuo and T. Yamamoto*103
Synthesis of (S)-(+)Pantolactone by M. Calmes, J. Daunis*, R. Jacquier and F. Natt107
Synthesis of 5'-Alkylamino- and 5'-Dialkylamino-5'-Deoxythymidine And 5'-Deoxy-xylo-Thymidine Analogs by W. Urjasz, L. Celewicz and K. Golankiewicz*109
Synthesis of 3-Vinylindoles from 3-Alkylideneindol-2(3H)-ones by E. M. Beccalli* and A. Marchesini113
A Safe and Convenient Procedure of Polyamines via Azide Intermediates by V. V. Martin, L. Lex and J. F. W. Keana*117
Improved Preparation of 2,5-Dimethyl-1,4-cyclohexanedione by M.-J. Queiroz, D. Joseph and G. Kirsch*120
Synthesis of 5-Bromo-3,3-diphenyl-1-pentene by R. A. Bunce* and R. S. Childress122
Palladium- and/or Copper-Mediated Cross-Coupling Reactions between 1-Alkynes and Vinyl, Aryl, 1 -Alkynyl, 1,2-Propadienyl, Propargyl and Allylic Halides or Related Compounds. A Review by R. Rossi*, A. Carpita and F. Bellina 127
Phosphorylated Adenine Derivatives as Potential Synthons for Antiviral Agents by M. El Masri and K. D. Berlin*161
"One pot" Synthesis of β-Functionalized Vinyl Azides through Addition of Tetramethytguanidinium Azide to Acetylenic and Allenic Compounds by F. Palacios*, D. Aparicio, J. M. de los Santos, I. P. de Heredia and G. Rubiales 171
Performance Fluids as an Inert Medium for the Preparation of Benzotfiazole Derivatives by A. R. Katritzky*, D. Toader and J. Jiang 179
Synthesis of Aminocyclobutane Mono- and Dicarboxylic Acids and Derivatives Thereof from (Phenylsulfonyl)bicyclobutanes by Y. Gaoni 185
OPPI Briefs (J.-P. Anselme, Editor) 213
A Novel Synthesis of a-Arylselenophosphorances by L. Wang, Z.-Z. Huang, H. Li and X. Huang*. 213
Coupling of Thiols and Selenols Catalyzed by Tris[trinitratocerium(IV)]parapefiodate by N. Iranpoor*, P. Salehi and F. Shiriny 216
An Improved Procedure for the Preparation of Aryloxiranes by L. W. Deady* and J. Desneves 219
Synthesis of Aldimines by Deoxygenation of Nittones by S. Sivasubramanian *, V. Ramamoorthy and G. Balasubramanian 221
Improved Preparations of Symmetric Porphyrins by L. Cheng* and J. Ma 224
Simple and Convenient Procedure for the Preparation of Acid Chlorides of Penicillins by E.G. Mata, C. E. Boschetti and O. A. Mascaretti*229
Preparation of 4-Chloro-2-thiophenecarboxylic Acid via Selective Bisulfite Salt Addition Procedure by J. W. ti!aggon*, J. M. Welborn, J. E. Godlewski, S. E. Kelly and T. G. LaCour 233
A New Efficient Synthesis of 3-Amino-1-phenylpyrrole by F. Fabis, P. Dallemagne, S. Rault and M. Robba*. 236
A Practical Method for the Synthesis of N-Fluorenylmethoxycarbonyl Diamines by M. Adamczyk* and J. Grote 239
Recent Progress in the Synthesis of Nitroarenes. A Review by B. P. Cho243
Synthesis and Analytical Aspects of the Chemistry of Piracetam-type Substituted Pyrrolidines. A Review by A. H. Gouliaev, J. B. Mønster, M. Vedsø and A. Senning*273
Naturally Occurring β-Lactones:Occurrence, Syntheses And Properties. A Review by C. Lowe and J. C. Vederas*305
The Preparation of Some Analogues of Myristoyl CoA by R. Pankayatselvan*, F. S. Guziec, Jr., A. S. Gopalan, R. Raghavachari, L. J. Guziec, D. Wei, R. L. Felsted and C. J. Glover347
Synthesis of 1-Arylcyclopropanecarbonitriles Under Phase-Transfer Catalytic Conditions by M. Fedorynski and A. Jonczyk*355
Preparation of Thiol Acids, Thiol Esters and Amides by Reactions of Carbonyl Sulfide with Grignard Reagents by A. R. Katritzky*, J.-L. Moutou and Z. Yang361
The Nickel(I) Catalyzed Coupling of a Diarylzinc with an Aryl Chloride in the Synthesis of Xenalipin by J. F. Eaddy367
OPPI Briefs (J.-P. Anselme, Editor)373
Facile Oxidative Decarboxylation of Aromatic α-Hydroxy Acids by Sodium Meta-periodate in the Presence of Dibenzo-[18]-Crown-6 and PTC by A. R. Kore, A. D. Sagar and M. M. Salunkhe*373
Solid-Phase Synthesis of a Peptide Comprising the 605-611 Disulfide Loop of GG41, Transmembrane Glycoprotein of Human Immunodeficiency Virus Type 1 (HIV-1) by G. G. Gevorkian*,M. Viveros,F. Zamudio,and C. Larralde 375
A Simple Preparation of Mono-tert-butyl Benzyloxycarbonyl-L-glutamates by M. Kempny, B. Rzeszotarska* and K. Pawelczak378
Further Applications of the Novel Synthesis of Arylthioglycolic Acids by Y. Yildirir* and A. Disli381
Acyl Main Group Metal and Metalloid Derivatives in Organic Synthesis. A Review by C. Nájera* and M. Yus*383
Alternate Preparation of α-Keto Esters from Acid Chlorides by A. R. Katritzky*, Z. Wang, A. P. Wells and P. J. Steel457
Reaction of 3-Sulfolenes with Conjugated Aldehydes and Ketones by R. Padmakumar, T. Subramanian and S. V. Bhat*463
An Efficient Synthesis of DAGO by P. A. Reddy, J. P. Hayes, A. H. Lewin and G. A. Brine*469
OPPI Briefs (J.-P. Anselme, Editor)475
Synthesis of New Polynitrostilbenes by X. Peng*, T. Chen, C. Lu and R. Sun475
Oxidative Cleavage of Ketoximes with Bentonitic Clay-Supported Copper (II) Nitrate by R. Sanabria*, P. Castañeda, R. Miranda, A. Tobón, F. Delgado and L. Velasco480
A Convenient Preparation of 1-Hydroperoxy-(1-p-nitrophenyl)ethanol by the Acid-catalyzed Oxidation of p-Nitroacetophenone with Hydrogen Peroxide by L. F. R. Cafferata* and J. C. Autino483
New Condensation Products of Diamines with 3-Ureidomethylenecoumarin by M. Hamdi and R. Sakellariou and V. Spéziale*487
A Novel Synthesis of Organic Diselenides by Z.-Z. Huang, F.-Y. Liu, J.-X. Du and X. Huang*492
A Convenient Preparation of Dibenzo[a,e]cyclooctatriene using Friedel-Crafts Intramolecular Acylation byT. Yamato*, H. Inoue, M. Fukumoto and M. Tashiro495
Improved Preparation of 2,5-Dimethyl-1,3-cyclohexanedione by D. Joseph, M.-J. Queiroz and G. Kirsch*499
An Improved Synthesis of 4'-Hydroxy- and 4'-Methoxybiphenyl-2-carboxylic Acids by G. Estenne, P. Dodey, P. Renaut and G. Leclerc*500
1-(Benzenesulfonyl)pyrrole-3-carboxaldehyde by D. Xiao and D. M. Ketcha*503
Liposomes Prepared from 2-[bis-(2-Hexacosa-10,12-diynoloxyethyl)amino]ethanesulfonic Acid by M. T. Holtzapple*, F. C. VanDuker, Jr., K. Y. Nam and J. J. Lalond507
A Superior Synthesis of Cholinergic Anabaseine by J. A. Zoltewicz* and M. P. Cruskie, Jr.510
A Practical Synthesis of 4-(3',4'-Dihydroxylphenyl)-1,2,3,4-tetrahydroisoquinoline by X. Zhao* and X. Wan513
Corrigenda517
Recent Advances in the Reactions of Hydrazines and Hydroxylamines with α,β-Unsaturated and β-Dicarbonyl Compounds. A Review by K. N. Zelenin519
B -Hydroxydiisopinocamphenylborane as a Mild, Chemoselective Reducing agent for Aldehydes by J. S. Cha*, E. J. Kim, O. O. Kwon, S. Y. Kwon, W. W. Seo and S. W. Chang541
OPPI Briefs (J.-P. Anselme, Editor)547
Synthesis of [1]Benzopyrano[3,4-h]benzo[b]-1,6-naphthyridine-6-ones by K. R. Prasad and M. Darbarwar*547
An Improved Synthesis of Fenbufen by R. Castillo*, M. Suárez-Herrera, M. Aparicio, F. Hernández-Luis and A. Hernández550
Improved Synthesis of Phenylacetamides by the Willgerodt Reaction with Microwave Heating by C. R. Strauss* and R. W. Trainor552
A Chemoenzymatic Synthesis of (R)-2-(1-Hydroxyethyl)-1,3-dithiane by F. Bracher* and T. Litz555
Chalcones by the Wittig Reaction of a Stable Ylide with Aldehydes Under Microwave Irradiation by C. Xu, G. Chen and X. Huang*559
A New, very short Preparation of 3-Benzoylcyclohexanone, a Key Building Block in Ketoprofen Synthesis by R. Ballini* and G. Bosica561
Ultrasonically Accelerated Syntheses of Furan-2,5-dicarbaldehyde from 5-Hydroxymethyl- 2-furfural by L. Cottier*, G. Descotes, J. Lewkowski and R. Skowroñski564
Improved Preparation of tris-(2-Furyl)phosphine by A. J. Zapata* and A. C. Rondon567
An Improved Procedure for the Preparation of 3-Methyl-2-cyclopenten-1-one by M. L. Karpinski, D. Nicholas and J. C. Gilbert*569
One-pot Synthesis of 4-[2-(3,4-Dichlorophenoxy)ethyl]-1-pentylpiperidine Hydrochloride by O. Axelsson* and D. Peters571
The Synthesis of Trimethylsilylmethoxymethyl Chloride by A. G. Schultz* and Y. Wang572
A Convenient Large-scale Preparation of endo-2-Methylbicyclo[2.2.1]hept-5-ene-exo- 2-carboxylic Acid by A. R. Katritzky*, Q. Hong, Z. Yang, D. J. Cundy and K. Brown-Wensley574
Sonication and Aluminum Amalgam in the Leimgruber-Batcho Reaction. An Improved Preparation of 6-Aminoindole by F. Dean Toste and I. W. J. Still*576
A Novel Synthesis of Triarylbismuth Disulfonates by L.-M. Jiang, Z.-Z. Huang and X. Huang*579
A Concise Synthesis of Pellitorine by J. E. Semple*582
A Large Scale Preparation of 1-Ethynylcyclopentene and 1-Hexen-4-yne by E. Davini*, M. Giongo* and M. Riocci*586
Trimethylsilyl Trichloroacetate as a Chloroform Alternative for the Synthesis of α-(Tricholoromethyl)-3-nitrobenzyl Alcohol by S. A. Weissman590
Synthesis of 1,3-Dimethylazulene by N. M. Irvine and M. Majewski*592
Synthesis of Acetoxylated and Hydroxylated Nitrobenzo[A]pyrene and Nitrobenzo[E]- pyrene by M.-J. Lee, J.-S. Lai, E. Cheng, and P. P. Fu*595
Large Scale Synthesis of 2-Chloro-5-fluoropyrimidine by A. Dunaiskis, T. Staigers, T. Keltonic, T. Chappie, C. Meltz, R. Dugger and M. A. Sanner*600
Cycloadditions of Azidoalkylcarboxylates to Acetylenes and Enamines. Regioselective Synthesis of Substituted Triazoles by F. Palacios*, A. M. Ochoa de Retana, J. Pagalday and J. M. Sánchez603
Novel Synthesis of Some Pyridinethione Nucleosides Related to 3-Deazauridine by A. M. E. Attia*, E. I. Ibrahim, F. E. A. Hay, M. M. A. Abbasi and H. A. E. Mansour613
Practical Synthesis and Characterization of 7-Benzylidenenaltrexone (BNTX) by A. H. Lewin*, M. R. Nilsson, J. P. Burgess and F. I. Carroll621
1,3-Dipolar Cycloaddition of Azidoalkylphosphonates and Carboxylates to Maleimide and Naphthoquinone by F. Palacios*, A. M. Ochoa de Retana and J. Pagalday625
A Synthesis of 4-α-Guanidino-2-deoxy-2,3-didehydro N-Acetylneuraminic Acid by J. Scheigetz*, R. Zamboni, M. A. Berstein and B. Roy637
OPPI Briefs (J.-P. Anselme, Editor)645
Regioselective Bromination of Cardanol Derivatives by O. A. Attanasi, S. Buratti and P. Filippone*645
Improved Synthesis of 2H-1,3(3H)-Oxazine-2,6-dione (Oxauracil) by G. M. Rehberg* and B. M. Glass651
Dibromantin as a Reagent for the Aromatic Bromination of Polyalkylbenzenes by X. Herault, P. Bovonsombat and E. Mc Nelis*652
An Improved Synthesis of 1-(2-Hydroxyethyl)uracil by B. Garnaik657
S<->RN1 Reactions in Liquid Ammonia at Room Temperature by P. G. Manzo, S. M. Palacios, R. A. Alonso* and R. A. Rossi*660
Facile Synthesis of 3-Chlorocoumarins by R. S. Mali* and J. V. Deshpande663
Preparation of New 4',5'-Disubstituted Benzocrown Ethers by H. Akkus and A. Gül*668
Preparation of 2-(2-Hydroxymethyl-6-methyl)phenylethanol by D. G. Tombari, A. G. Moglioni, and G. Y. M. Iglesias*671
A Convenient Synthesis of SMALLDELTA-Coniceine by N. De Kimpe*, E. Stanoeva, A. Georgieva, M. Keppens and O. Kulinkovich674
Synthesis of Pyrazino(3,2,1-j,k)carbazole Derivatives by K. J. R. Prasad*, C. S. Vijayalakshmi and D. Sowmithran678
An Efficient Synthesis of (S)-(+)-2-Tridecanol Acetate, an Aggregation Pheromone of Drosophila Mulleri by F. Bracher* and B. Schulte682
Synthesis of 3- and 3,3'-Substituted 1,2'-Bi-2-naphthols by J. Li, W. Li, Y. Li, Y. Li and S. Yang685
Synthesis of a Spirocyclic Oxindole Analogue as a Putative Replacement for Pro2-pro3-gly4-phe5 in Bradykinin Antagonists by R. R. Goehring691
A Practical Synthesis of 4-Bromo-2-cyano-3-methyl-2-butenenitrile by L. S. Newton, S. Chan, B. J. Sitter, S. J. Brenek, J. W. Raggon and T. F. Braish*695
New Method for the Preparation of Guanylthioureas by P. Tari* and A. Gajary697
An Improved Synthesis of 3-(2,5-Dimethoxybenzyl)pyrrole by C. Aquino-Binag, N. Kumar* and P. Pigram700
Oxidation of Various Alcohols with in situ Generated Montmorillonite K10-supported Ferric Nitrate Reagent in an Aprotic Solvent by M. Hirano, K. Komiya and T. Morimoto*703
An Improved Synthesis of Dimethyltitanocene by J. F. Payack*, D. L. Hughes*, D. Cai, I. F. Cottrell, and T. R. Verhoeven707
(±)-3,4,4a,5,6,7-Hexahydro-4a,7,7-trimethyl-1(2H)-naphthalenone by R. A. Bunce* and R. S. Childress709
Corrigendum715
INDEXES717

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