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Abstract
Synth. Commun. 2004, 34, 2697
A Simple and Efficient Synthesis of N‐[2‐{(4‐Propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a Tyrosine‐Dependent Cytotoxic Agent as a Topical Antimelanoma Therapy
Lisa D. Coutts,1 Harold Meckler,1 and Karl F. Popp2
1Albany Molecular Research, Inc., Albany, New York, USA
2August C. Stiefel Research Institute, Inc., Oak Hill, New York, USA
The synthesis of N‐[2‐{(4‐propionyloxyphenyl)thio}ethyl]propionamide (DIPCAP), a tyrosine‐dependent cytotoxic agent that is currently being evaluated as a topical antimelanoma treatment is described. Problems encountered in scaling up the original patent procedure have been eliminated and N‐[2‐{(4‐propionyloxyphenyl)thio}ethyl]propionamide was obtained in an overall yield of 65% from commercially available starting materials.
Abstract
Synth. Commun. 2004, 34, 2705
Infrared Irradiation: Effective Promoter in the Formation of N‐Benzylideneanilines in the Absence of Solvent
Miguel Á. Vázquez,1 Miguel Landa,1 Leonor Reyes,1 René Miranda,2 Joaquín Tamariz,1 and Francisco Delgado,1
1Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación Carpio y Plan de Ayala, 11340 México, DF, Mexico
2Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Av. 1ro de Mayo s/n, esquina con Avenida del Vidrio, Colonia Santa María de las Torres, Cuautitlán Izcalli, Estado de México, CP 54740, Mexico
Infrared irradiation promoted the formation of a series of Schiff bases (3a–3z) by condensation of benzaldehydes (1a–1e) with various anilines (2a–2c), in the absence of solvent.
Abstract
Synth. Commun. 2004, 34, 2719
Friedel‐Crafts Reaction of Activated Benzene Rings with Captodative and Electron‐Deficient Alkenes. A One‐Step Synthesis of the Natural Product Methyl 3‐(2,4,5‐Trimethoxyphenyl)Propionate
Raúl Aguilar, Adriana Benavides, and Joaquín Tamariz
Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Carpio y Plan de Ayala, México, D.F., Mexico
Abstract
Synth. Commun. 2004, 34, 2737
Synthesis of N‐octyl‐2,7‐dimethoxy‐1,8‐bistrimethylsilyl‐3,6‐dibromocarbazole
Jimmy Bouchard, Salem Wakim, and Mario Leclerc
Département de Chimie, Université Laval, Quebec City, Canada
Starting with 2,7‐dimethoxycarbazole, a N‐octyl‐2,7‐dimethoxy‐1,8‐bistrimethylsilyl‐3,6‐dibromocarbazole derivative has been synthesized in only three steps with good overall yields.
Abstract
Synth. Commun. 2004, 34, 2743
Solid‐Phase Synthesis of N‐Aryl‐N′‐Carboalkoxy Guanidines by the Mitsunobu Reaction of Fmoc‐Guanidines
Dale E. Robinson, Punit P. Seth, and Elizabeth A. Jefferson
Ibis Therapeutics, A Division of Isis Pharmaceuticals, Inc., 2292 Faraday Avenue, Carlsbad, California, USA
Abstract
Synth. Commun. 2004, 34, 2751
A Mild and Efficient Method for Cleavage of C˭N Using Imidazolium Dichromate
Surya Kanta De
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy, Purdue Cancer Center, Purdue University, West Lafayette, Indiana, USA
Abstract
Synth. Commun. 2004, 34, 2757
A Regioselective Synthesis of Tetrahydrobenzodiazepin‐5‐ones via The Schmidt Rearrangement of Quinolones
Ricardo A. Tapia and Cesar Centella
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla, Santiago, Chile.
The regioselective synthesis of 2,3,4,5‐tetrahydro‐1H‐1,4‐benzodiazepin‐5‐ones by the Schmidt rearrangemet of 1,2,3,4‐tetrahydro‐4‐quinolones with oxygen substituents at C‐8 is described.
Abstract
Synth. Commun. 2004, 34, 2767
A Facile Method for the Preparation of Pure cis‐2,4‐Pentanediol
Lisa Bonner, Stewart Frescas, and David E. Nichols
Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, 575 Stadium Mall Drive, West Lafayette, Indiana
Purification of cis‐2,4‐pentanediol via thermodynamic acetal formation with acetophenone.
Abstract
Synth. Commun. 2004, 34, 2773
Practical Sulfonylation of Amines with 4‐Hydroxybenzenesulfonyl Chloride: in situ Silylation–Desilylation
Jeremy I. Levin, Mila T. Du, and Kaapjoo Park
Wyeth Research, 401 N. Middletown Rd., Pearl River, New York, USA
A one‐pot procedure for the efficient sulfonylation of amines with 4‐hydroxybenzenesulfonyl chloride involving in situ protection and deprotection of the phenol with N,O‐bis‐ (trimethylsilyl)acetamide is presented.
Abstract
Synth. Commun. 2004, 34, 2783
A Novel and Simple Solvent Free Method for Nucleophilic Aromatic Substitution of Inactive Aryl Halides
Mohammed M. Hashemi, and Maryam Akhbari
Department of Chemistry, Sharif University of Technology, Tehran, Iran
A simple, high yield, and short time method for nucleophilic displacement reaction of inactive aryl halides is reported. The reaction is performed in microwave oven under thermal condition with montmorillonite supported AgNO3.
Abstract
Synth. Commun. 2004, 34, 2789
Highly Regioselective Ring Opening of Epoxides with Polymer Supported Phenoxide And Naphthoxide Anions
B. Tamami, N. Iranpoor, and R. Rezaei
Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iran
Polymer supported phenoxide and naphthoxide anions are used for regioselective ring opening reactions of epoxides to give aryl‐ether alcohols in high yields under mild reaction conditions.
Abstract
Synth. Commun. 2004, 34, 2797
Synthesis of 2‐Hydroxybenzophenones by Oxidation of 3‐Aryl‐3H‐Benzofuran‐2‐Ones
Peter Nesvadba, Lucienne Bugnon, and Marvin Scheffel
Ciba Specialty Chemicals Inc., CH‐4002 Basel, Switzerland
Abstract
Synth. Commun. 2004, 34, 2803
Microwave Irradiated Solventless Sonogashira Reaction on Nickel(0) Powder Doped KF/Al2O3
Min Wang,1 Pinhua Li,1 and Lei Wang1,2
1Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui, P.R. China
2State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P.R. China
A microwave irradiated solventless Sonogashira coupling reaction catalyzed by nanosize nickel(0) powder on potassium fluoride–alumina mixture has been developed.
Abstract
Synth. Commun. 2004, 34, 2813
N‐Acyliminium Reagents of 3,4‐Dihydro‐β‐carboline and Acyl Chlorides in the Reaction of Intermolecular α‐Amidoalkylation Toward Heteroaromatics
Atanaska K. Donova, Stela M. Statkova‐Abeghe, Atanas P. Venkov, and Iliyan I. Ivanov
Department of Organic Chemistry, University of Plovdiv, Plovdiv, Bulgaria
N‐Acyliminium reagents 3 of 3,4‐dihydro‐β‐carboline 1 with acyl chlorides were successfully used in reaction of α‐amidoalkylation toward heterocyclic aromatics for preparation of 1‐heteroaryl‐2‐acyl‐2,3,4,9‐tetrahydro‐β‐carbolines 4.
Abstract
Synth. Commun. 2004, 34, 2823
Titanium Dioxide as a Mild and Efficient Catalyst for Conversion of Epoxides to Thiiranes
Bahram Yadollahi,1 Shahram Tangestaninejad,2 and Mohammad Hossein Habibi2
1Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P.O. Box 45195‐159, Gava Zang, Zanjan, Iran.
2Department of Chemistry, Esfahan University, Esfahan, Iran
TiO2 efficiently catalyze the reaction of a variety of epoxides with ammonium thiocyanate in refluxing acetonitrile to afford the corresponding thiirane in high to excellent yields.
Abstract
Synth. Commun. 2004, 34, 2829
Acid‐Catalysed Selective Monoiodination of Electron‐Rich Arenes by Alkali Metal Iodides
M. A. Pasha1 and Yi Yi Myint2
1Department of Chemistry, Central College Campus, Bangalore University, Bangalore, India
2Department of Chemistry, Yadanabon University, Myanmar
The reaction of electron rich arenes with alkali metal iodides such as sodium and potassium iodides in the presence of acid gave p‐iodoarenes in high yields.
Abstract
Synth. Commun. 2004, 34, 2835
Oxidation of Benzylic Alcohols to Carbonyl Compounds with Potassium Permanganate in Ionic Liquids
Anil Kumar, Nidhi Jain, and S. M. S. Chauhan
Department of Chemistry, University of Delhi, Delhi, India
The selective oxidation of primary and secondary benzylic alcohols with potassium permanganate in ionic liquids to give corresponding aldehydes and ketones in 83–97% yields has been described.
Abstract
Synth. Commun. 2004, 34, 2843
Efficient Reduction of tetrakis(2‐Cyanoethyl)cyclen with Sodium–Toluene and Synthesis of Carboxymethyl‐ and Hydroxyethyl Functionalized Second Generation Pendant Arms Appended Cyclens
B. Jebasingh and V. Alexander
Department of Chemistry, Loyola College, Chennai, India
Efficient reduction of tetrakis(2‐cyanoethyl)cyclen with sodium–toluene into tetrakis(3‐aminopropyl)cyclen and the subsequent alkylation of the latter to give carboxymethyl‐ and hydroxyethyl‐functionalized second generation pendant arm appended cyclens have been reported.
Abstract
Synth. Commun. 2004, 34, 2849
Potassium Fluoride Assisted Selective Acetylation of Alcohols with Acetic Acid
J. W. John Bosco, B. Rama Raju, and Anil K. Saikia
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, India
Potassium fluoride promotes the acetylation of primary and secondary alcohols with acetic acid in excellent yield. Phenols are not affected under these reaction conditions. The groups like double bond, chloro, methoxy, benzyloxy, thiol, and nitro remain unaffected.
Abstract
Synth. Commun. 2004, 34, 2857
Aminoalkylation of 10‐Hydroxycamptothecin Using Methylene Chloride under Solid–Liquid Phase Transfer Catalysis: A New Approach for the Preparation of Topotecan
S. C. Puri, G. Handa, K. L. Dhar, O. P. Suri, and G. N. Qazi
Natural Products Chemistry Division, Regional Research Laboratory (CSIR), Jammu 180004, India
The use of dichloromethane as a reagent, for the preparation of Topotecan {(4S)‐10‐(dimethylamino)methyl‐4‐ethyl‐4,9‐dihydroxy‐1‐H‐pyrano[3,4:6,7]indolizino‐[1,2‐b]quinoline‐3,14(4H,12H) dione} from 10‐hydroxy‐camptothecin under solid–liquid phase transfer catalysis, which behaves both as a solvent and a reagent serving as for C‐1 unit source for aminoalkylation of 10‐hydroxy‐ (4S) camptothecin.
Abstract
Synth. Commun. 2004, 34, 2863
Selective Reduction of Aldehydes to Alcohols Using Alumina with a Catalytic amount of Base Under Microwave Irradiation
Prasun K. Pradhan, Parasuraman Jaisankar, Bikash Pal, Sumit Dey, and Venkatachalam S. Giri
Department of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata, India
