Graphical Abstracts

Abstract

Synth. Commun. 2004, 34, 2313

Synthesis of Peptidyl Ureas Using p‐Nitrophenyl‐(9‐Fluorenylmethoxycarbonylamino) Methyl Carbamate

Basanagoud S. Patil, Ganga‐Ramu Vasanthakumar, and V. V. Suresh Babu*

Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore, India

An efficient synthesis of p‐nitrophenyl‐(9‐fluorenylmethoxycarbonylamino)methyl carbamate derivatives and their utility for the preparation of dipeptidyl ureas has been described.

Abstract

Synth. Commun. 2004, 34, 2323

Synthesis of (−)‐Mintlactone via Intramolecular Wittig– Horner Reaction

Rajesh K. Pandey, Rajesh K. Upadhyay, Sandip S. Shinde, and Pradeep Kumar*

Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, India

An efficient synthesis of (−)‐mintlactone has been described starting from (+)‐pulegone and employing the intramolecular Wittig‐Horner reaction as the key step.

Abstract

Synth. Commun. 2004, 34, 2331

A Simple System For Preparation of Protected Glycosidic Carbohydrate Nitriles from Corresponding Oximes

Vikas N. Telvekar* and Krishnacharya G. Akamanchi*

Department of Pharmaceutical Sciences and Technology, U.I.C.T, Matunga, Mumbai, India

Glycosidic nitriles of protected carbohydrates were prepared efficiently and rapidly from the corresponding oximes using thionyl chloride/benzotriazole combination as dehydrating system.

Abstract

Synth. Commun. 2004, 34, 2337

Reductive Cleavage of S–S Bond by Zn/AlCl₃ System: A Novel Method for the Synthesis of Sulfides from Alkyl Tosylates and Disulfides

Barahman Movassagh* and Amir Mossadegh

Department of Chemistry, K. N. Toosi University of Technology, Tehran, Iran

Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl₃ in aqueous media to yield zinc thiolates. These thiolate anion species then react with alkyl tosylates to give sulfides in high to excellent yields.

Abstract

Synth. Commun. 2004, 34, 2345

The Effect of Co‐catalyst in the Friedel–Crafts Reaction in Synthesis of Diaryl‐naphth‐1‐yl‐methane Derivatives

S. Ray, Neeta Srivastava, Sangita, and Atul Kumar*

Division of Medicinal Chemistry, Central Drug Research Institute, Lucknow, India

Abstract

Synth. Commun. 2004, 34, 2359

A Convenient Method for the Oxidation of Aromatic Amines to the Nitro Compounds Using Tetra‐n‐alkyl Ammonium Bromates

Satya Sandhya Das, Utpal Nath, Dibakar Deb, and Pranab J. Das*

Department of Chemistry, Gauhati University, Guwahati, India

Tetra‐n‐alkylammoniumbromate prepared and used for the oxidation of aromatic amines to nitro compounds. Work up easy and products obtained in high yield

Abstract

Synth. Commun. 2004, 34, 2365

Chemistry of L‐Ascorbic Acid. IV. Regioselective O‐Alkylation of 5,6‐O‐Isopropylidene‐L‐Ascorbic Acid Using CsF

Mukund G. Kulkarni* and Sandesh D. Kate

Department of Chemistry, University of Pune, Pune, India

The regioselective 3‐O‐alkylation of 5,6‐O‐isopropylidene‐L‐ascorbic acid is achieved under mild conditions using CsF as a base.

Abstract

Synth. Commun. 2004, 34, 2371

A Short Enantioselective Synthesis of (R)‐(+)‐γ‐Jasmolactone

Giuliano C. Clososki, Lauri J. Missio, and João V. Comasseto*

Instituto de Química, Universidade de São Paulo, São Paulo, SP, Brazil

(R)‐(+)‐γ‐Jasmolactone (1b) was prepared in two steps starting from the easily prepared (S)‐(−)‐(2).

Abstract

Synth. Commun. 2004, 34, 2379

A Simple Synthesis of Photolabile α‐Methyl Nitrobenzyl Compounds

Charles P. Salerno, Henderson J. Cleaves

The Scripps Institution of Oceanography, UCSD, La Jolla, California, USA

Abstract

Synth. Commun. 2004, 34, 2387

Zirconium(IV) Chloride Mediated Cyclodehydration of 1,2‐Diacylhydrazines: A Convenient Synthesis of 2,5‐Diaryl 1,3,4‐Oxadiazoles

G. V. M. Sharma,* Asra Begum, Rakesh, and Palakodety Radha Krishna

Discovery Laboratory, Organic Chemistry Division‐III, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Synth. Commun. 2004, 34, 2393

Facile Synthesis of Aminoalcohols by Ring Opening of Epoxides Under Solvent Free Conditions

Gloria Huerta,¹ Guadalupe Contreras‐Ordoñez,¹ C. Alvarez‐Toledano,¹ Víctor Santes,² Elizabeth Gómez,^1,* and Rubén A. Toscano¹

¹Instituto de Química‐UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán, México DF México

²Instituto Mexicano del Petróleo, Programa de Tratamiento de Crudo Maya, Col. San Bartolo Atepehuacan, México, DF México

Abstract

Synth. Commun. 2004, 34, 2407

Efficient Synthesis of Doxorubicin Melanotransferrin p97 Conjugates Through SMCC Linker

Qingqi Chen* and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., Novato, California, USA

Abstract

Synth. Commun. 2004, 34, 2415

Synthesis of Camptothecin Melantotransferrin (p97) Conjugate Through a Carbamate Bond

Qingqi Chen* and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., Novato, California, USA

Abstract

Synth. Commun. 2004, 34, 2425

Efficient synthesis of polyethylene glycol mono‐carboxylate via Michael conjugate addition

Qingqi Chen* and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., Novato, Novato, California, USA

Mono‐carboxylated poly(ethylene glycol) (PEG), the very useful precursors for the synthesis of the PEG derived heterobifuncational linkers, are synthesized in high yield in one‐pot via Michael conjugate addition of acrylate esters with PEG and catalyst amount of sodium in THF.

Abstract

Synth. Commun. 2004, 34, 2433

Stereochemical Studies of Chiral Acyclic Nitroxides Coupling with a Prochiral Radical

Rebecca Braslau,^1,* Vladimir Chaplinski,¹ Aaron Nilsen,¹ and Navamoney Arulsamy²

¹Department of Chemistry and Biochemistry, University of California, Santa Cruz, California, USA

²Department of Chemistry, University of Wyoming, Laramie, Wyoming, USA

A series of acyclic chiral nitroxides bearing a hydrogen atom on the carbon adjacent to the nitroxide nitrogen was investigated for stereoselectivity in a coupling reaction with the prochiral radical 1‐phenethyl. In one case, an x‐ray structure of the major diastereomer was obtained, which corroborates a model for predicting the stereoselectivity.

Abstract

Synth. Commun. 2004, 34, 2443

Chloromethyl sulfones from sulfonyl chlorides via a one‐pot procedure

Schuyler Antane,* Ronald Bernotas, Yanfang Li, Robert McDevitt, and Yinfa Yan

Chemical and Screening Sciences, Wyeth Research, Princeton, New Jersey, USA

A simplified one‐pot transformation of a diverse set of aryl‐ and heteroaryl‐sulfonyl chlorides into the corresponding chloromethyl sulfones is described.

Abstract

Synth. Commun. 2004, 34, 2451

Regiospecific Synthesis of 5‐Halosubstituted Thiophene Pyridyl Thiourea Compounds as Non‐Nucleoside Inhibitors of HIV‐1 Reverse Transcriptase

T. K. Venkatachalam^1,2 and F. M. Uckun^2,3,4,*

¹Department of Chemistry, Parker Hughes Institute, Roseville, Minnesota, USA

²Drug Discovery Program, Parker Hughes Institute, Roseville, Minnesota, USA

³Department of Immunology and ⁴Department of Virology, Parker Hughes Institute, Roseville, Minnesota, USA

The regiospecific synthesis of 5‐halo thiophene ethylamines and halosubstituted phenylethyl thioureas was accomplished in five steps with an overall yield of 45–60%. The bromo‐substituted chloropyridyl thiourea compounds N‐[2‐(5‐Bromothiophene ethyl)]‐N′‐[2‐(5‐chloropyridyl)]thiourea (compound PHI‐2002) and N‐[2‐(5‐iodothiophene ethyl)]‐N′‐[2‐(5‐chloropyridyl)]thiourea (compound PHI‐2020) were the most active agents and inhibited recombinant HIV‐1 RT at nanomolar concentrations.

Abstract

Synth. Commun. 2004, 34, 2463

Synthesis of β‐fluorophenethyl halopyridyl thiourea compounds as non‐nucleoside inhibitors of HIV‐1 reverse transcriptase

T. K. Venkatachalam^1,2 and F. M. Uckun^2,3,4,*

¹Department of Chemistry, Parker Hughes Institute, Roseville, Minnesota, USA

²Drug Discovery Program, Parker Hughes Institute, Roseville, Minnesota, USA

³Department of Virology and ⁴Department of Immunology, Parker Hughes Institute, Roseville, Minnesota, USA

Synthesis of β‐fluorophenethylamines was accomplished in three steps with an overall yield of 50%. Condensation of β‐fluorophenethylamine hydrochloride with thiocarbonyl imidazole derivative derived from halopyridyl amines in dimethylformamide furnished the required thiourea compounds as crystalline solids. Several of the β‐fluorophenethyl thiourea compounds inhibited HIV‐1 reverse transcriptase (RT) at nanomolar to low micromolar concentrations.

Abstract

Synth. Commun. 2004, 34, 2473

An efficient synthesis of the ace inhibitor [phenyl‐³H] lisinopril

Judith A. Egan and Crist N. Filer*

PerkinElmer Life and Analytical Sciences Inc., Boston, Massachusetts

An effective synthesis of [³H] lisinopril at high specific activity is described.

Abstract

Synth. Commun. 2004, 34, 2479

Efficient tetrahydrosalen synthesis from Mannich‐type bases

Augusto Rivera,* Rodolfo Quevedo, Miguel A. Navarro, and Mauricio Maldonado

Departamento de Química, Universidad Nacional de Colombia, Apartado Aéreo, Ciudad Universitaria, Bogotá, Colombia

Abstract

Synth. Commun. 2004, 34, 2487

Synthesis of 5‐Alkyl‐2,3‐dihydro‐1,4‐benzodioxins

Adriano Martendal, Rafael Dias, Faruk Nome, and César Zucco

Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, Brazil

A series of 5‐alkyl‐2,3‐dihydro‐1,4‐benzodioxins has been synthesized by intramolecular cyclization of 2‐(2‐bromoethoxy)‐3‐alkylphenols prepared from 2‐alkylphenols.

Abstract

Synth. Commun. 2004, 34, 2499

Synthesis of Glucopyranosyl Amides Using Polymer‐Supported Reagents

Yuriko Y. Root,¹ Maximillian S. Bailor,² and Peter Norris^1,*

¹Department of Chemistry, Youngstown State University, Youngstown, Ohio, USA

²Department of Chemistry, Grinnell College, Grinnell, Iowa, USA

Glucopyranosyl amides are formed from a glucosyl Staudinger‐type process