Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 2377

Synthesis of Doxorubicin Conjugates Through Hydrazone Bonds to Melanotransferrin P97

Qingqi Chen,* Damian A. Sowa, Jianlin Cai, and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., 46 Galli Drive, Novato, CA 94949, USA

Through hydrazone bonds, three doxorubicin-p97 conjugates 5, 9, 12 are synthesized using adipic dihydrazine, 4-(4-N-maleimidophenyl)-butyric acid hydrazine 6 and adipic acid mono hydrazine 10 as linkers. These are potential agents for treating brain tumors.

Abstract

Synth. Commun. 2003, 33, 2391

Synthesis of Doxorubicin Conjugates Through 14-Hydroxy Group to Melanotransferrin P97

Qingqi Chen,* Damian A. Sowa, and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., 46 Galli Drive, Novato, CA 94949, USA

Using Fmoc to protect the amino group, Fmoc-doxorubicin is conjugated through the 14-hydroxy group to the amino group of melanotransferrin p97 by spacer arms such as succinate and glutarate. The Fmoc group is then removed under basic conditions, which affords doxorubicin-p97 conjugates. The resulting bioconjugates are potential agents for treating brain tumors.

Abstract

Synth. Commun. 2003, 33, 2401

Efficient One-Pot Synthesis of Doxorubicin Conjugates Through its Amino Group to MeLaNotransferrin P97

Qingqi Chen,* Damian A. Sowa, Jianlin Cai, and Reinhard Gabathuler

Biomarin Pharmaceutical Inc., 46 Galli Drive, Novato, CA 94949, USA

Abstract

Synth. Commun. 2003, 33, 2423

Preparation of Ethyl 5-Iodo-1H-indole-2-carboxylate

Douglas C. Beshore* and Christopher J. Dinsmore

Merck Research Laboratories, Department of Medicinal Chemistry, Sumneytown Pike, West Point, PA 19486, USA

A facile, two step procedure for the preparation of ethyl 5-iodo-1H-indole-2-carboxylate (1) from commercially available ethyl 1H-indole-2-carboxylate is described herein, employing a regioselective C3, C5-bisiodination followed by zinc-mediated C3-dehalogenation.

Abstract

Synth. Commun. 2003, 33, 2429

Syntheses and Characterizations of Imidazole-4,5-diacylhydrazones

Guifa Su,* Jiangke Qin, Qingling Ni, and Hongtao Mu

Department of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, 541004, P.R. China

Seven titled compounds were synthesized via 4 steps in about 24% overall yield are described.

Abstract

Synth. Commun. 2003, 33, 2437

An Improved Synthetic Method of 1-Chloro-7-methoxy-9H-thioxanthen-9-One

Hua-Zhong He and Chul-Hoon Kwon*

Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, St. John's University, Jamaica, New York 11439, USA

1-Chloro-7-methoxy-9H-thioxanthen-9-one (3) was prepared via cyclization of 2-chloro-6-(4-methoxyphenylthio)-benzonitrile (1) in a one pot, two step reaction with improved yield (60%) over the previous literature report.

Abstract

Synth. Commun. 2003, 33, 2441

One Step Synthesis of N-[1-(2-Diethylamino-ethylamino)-7-(H or methoxy)-9-oxo-9H-thioxanthen-4-ylmethyl]-formamides and, Acetamide from Their Corresponding Alcohols, Hycanthone, and 7-Methoxy-hycanthone

Hua-Zhong He and Chul-Hoon Kwon*

Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, St. John's University, Jamaica, New York 11439, USA

N-[1-(2-Diethylamino-ethylamino)-7-(H or methoxy)-9-oxo-9H-thioxanthen-4-ylmethyl]-formamides and acetamide were synthesized from their corresponding alcohols, hycanthone and 7-methoxy-hycanthone, in one step procedure and 45% yield.

Abstract

Synth. Commun. 2003, 33, 2447

Efficient Synthesis of a Complete Donor/Acceptor bis(Aryl)diyne Family

Brian T. Holmes,¹ William T. Pennington,^1,* and Timothy W. Hanks^2,*

¹Department of Chemistry, Hunter Chemistry Laboratories, Clemson University, 223 South Palmetto Drive, Clemson, South Carolina, 29634-0973 USA

²Department of Chemistry, Furman University, 3300 Poinsett Hwy., Greenville, South Carolina, USA

Abstract

Synth. Commun. 2003, 33, 2463

Synthesis, Characterization, and Utility of Trialkyl(3-Sulfopropyl)Ammonium Betaines as New Phase Transfer Reagents

Joseph Paul Jayachandran¹ and Maw-Ling Wang^2,*

¹Department of Chemical Engineering, National Chung Cheng University, Chiayi, Taiwan 621, R.O.C.

²Department of Chemical Engineering, Tung Hai University Taichung, Taiwan 407, R.O.C.

Synthesis of water-soluble phase transfer reagents, triethyl(3-sulfopropyl)ammonium betaine [QS-1], tributyl(3-sulfopropyl)ammonium betaine [QS-2], and its utility in various hydroxide-ion initiated reactions are described.

Abstract

Synth. Commun. 2003, 33, 2469

Effective Mechanochemical Synthesis of [60]Fullerols

Pu Zhang,^1,2 Hualong Pan,³ Dongfang Liu,¹ Zhi-Xin Guo,^1,* Fushi Zhang,³ and Daoben Zhu¹

¹Institute of Chemistry, and ²Graduate School, Chinese Academy of Sciences, No. 2 Zhongguang Cun Road 1(N), Beijing 100080, China

³Department of Chemistry, Tsinghua University, Beijing 100084, China

[60]Fullerols were synthesized effectively in high yield under the high-speed vibration milling (HSVM) conditions in air at room temperature.

Abstract

Synth. Commun. 2003, 33, 2475

A Novel and Efficient Synthesis of (6R,7R)-7-Amino-3-hydroxymethyl Cephalosporanic Acid: A Versatile Precursor of Cefuroxime Acid

Santosh Kumar Singh,¹ R. P. Tiwari, and Praveen Jain^2,*

¹Verdayani Society, Flat No. 1, Sakalroop Garden, Sus Road, Pashan, Pune 411-021, MH, India

²Government M. L. B. Girls P. G. College, Bhopal 462 003, MP, India

Synthesis of 7-AHCA 4 from 3 by reacting with TBAH and exploitation to the synthesis of cefuroxime acid and its sodium salt 7.

Abstract

Synth. Commun. 2003, 33, 2483

Zinc Mediated Alkylation of Cyclic Secondary Amines

M. S. R. Murty,* B. Jyothirmai, Palakodety Radha Krishna, and J. S. Yadav

D-202, Discovery Laboratory, Organic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500 007, India

Zinc metal mediated simple and efficient alkylation of cyclic secondary amines e.g., piperazines and morpholine with allyl bromide, chlorobromo propane, and p-methoxy benzyl bromide is described in good yields.

Abstract

Synth. Commun. 2003, 33, 2487

Chemo-Enzymatic Preparations of (R)- and (S)-3-Iodocyclohex-2-en-1-yl Acetate

J. P. Barnier and L. Blanco*

Laboratoire des Carbocycles (Associé au CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bât. 420, Université de Paris-Sud, 91405 Orsay, France

Inversion of the alcohol chirality was performed without separation from the optically active ester.

Abstract

Synth. Commun. 2003, 33, 2497

Clay Supported Ammonium Nitrate “Clayan”: A New Reagent for Selective Nitration of Arenes

H. M. Meshram,^1,* Y. S. S. Ganesh,¹ A. V. Madhavi,¹ B. Eshwaraiah,¹ J. S. Yadav,¹ and D. Gunasekar²

¹Indian Institute of Chemical Technology, Tarnaka, Hyderabad, Andhra Pradesh, 500 007, India

²Department of Chemistry, S. V. University, Tirupati, Andhra Pradesh, India, 517 502

Selective nitration of a number of functionalized arenes is described.

Abstract

Synth. Commun. 2003, 33, 2505

A New Method for the Synthesis of Organosulfur Tri-fluorides

V. E. Pashinnik, E. G. Martyniuk, M. R. Tabachuk, Yu. G. Shermolovich,* and L. M. Yagupolskii

Institute of Organic Chemistry of the NAS of Ukraine, Murmanska, 5, Kyiv 02094, Ukraine

The method of the different types of organosulfur trifluorides consists in the reaction of thiosulfurous acid diamides, diaryldisulfides or diheteryldisulfides with chlorine in the presence of potassium fluoride excess.

Abstract

Synth. Commun. 2003, 33, 2511

The Palladium Catalyzed Hydrostannation of 1-AlkEnylphosphonates: A New Approach to Stereodefined α,β-disubstituted Vinylphosphonates

Xian Huang,^1,2,* and Zheng-Chang Xiong¹

¹Department of Chemistry, Zhejiang University, Xixi Campus, Tianmushan Road, Hangzhou 310028, P.R. China

²State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P.R. China

Abstract

Synth. Commun. 2003, 33, 2519

A Convenient One-Pot Completely Stereoselective Synthesis of trans-4-Hydroxystilbenes and its Derivatives and X-Ray Structure of its Precursor

Rakeshwar B. Chhor,¹ Kunwar A. Singh,² B. Nosse,¹ and Vishnu K. Tandon^2,*

¹Institut fur Organische Chemie, Universitat Regensburg, Regensburg, Germany

²Department of Chemistry, Lucknow University, Lucknow 226007, India

The synthesis of E-isomer of 4-hydroxystilbene and its derivatives 3 by reductive elimination of the carbonyl function in 2-phenyl-1-(4-hydroxyphenyl)ethan-1-one and its derivatives 2 and the X-ray structure of 2a are described.

Abstract

Synth. Commun. 2003, 33, 2531

An Alternative Method for the Highly Selective Iodination of Alcohols Using a CSI/BF₃·Et₂O System

Safdar Hayat, Atta-ur-Rahman, Khalid Mohammed Khan,* M. Iqbal Choudhary, Ghulam Murtaza Maharvi, Zia-Ullah, and Ernst Bayer

International Center for Chemical Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi 75270, Pakistan

A variety of allylic and benzylic alcohols have been converted into the corresponding iodides using cesium iodide (CsI) in the presence of boron trifluoride etherate (BF₃Et₂O) in acetonitrile under mild conditions.

Abstract

Synth. Commun. 2003, 33, 2541

An Expeditious and Convenient One Pot Synthesis of 2,5-Disubstituted-1,3,4-Oxadiazoles

Sabir H. Mashraqui,* Shailesh G. Ghadigaonkar, and Rajesh S. Kenny

Department of Chemistry, University of Mumbai, Vidyanagari, Santacruz (E), Mumbai 400098, India

A one pot convenient procedure is described for the synthesis of 2,5-disubstituted-1,3,4-oxadiazoles in HMPA solvent under microwave irradiation.

Abstract

Synth. Commun. 2003, 33, 2547

Controlled Acetolysis of 3,6-Anhydro-5-o-benzyl-1,2-o-Isopropylidene-α-d-glucofuranose: Synthesis of 1-(3′,6′-Anhydro-α-d-glucofuranosyl)thymine

Hari Babu Mereyala* and Pallavi Pola

Organic Chemistry Division III, Indian Institute of Chemical Technology, Hyderabad 500 007, India

Synthesis of α-linked nucleoside 7 is described.

Abstract

Synth. Commun. 2003, 33, 2553

Synthesis and Resolution of Dinucleotide(TpAZT) Phosphoramidates

Changxue Lin,¹ Hua Fu,^1,* Guangzhong Tu,² and Yufen Zhao^1,*

¹The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Tsinghua East Road, Beijing 100084, P.R. China

²Beijing Institute of Microchemistry, Beijing 100091, P.R. China

Dinucleotide (TpAZT) phosphoramidates were synthesized through Atherton-Todd reaction of dinucleoside H-phosphonates and amino acid methyl esters, and their diastereomers (R_p and S_p) were separated by crystallization.

Abstract

Synth. Commun. 2003, 33, 2563

Synthesis of Novel Chiral C₂-Symmetric Bisoxazoline Ligands Containing 2,5-Di(m-Substituted)phenyl-1,3,4-Oxadiazole

Dong-Cheng Xu, Da-Ming Du,* Nan Ji, Zhan-Yue Wang,^# and Wen-Ting Hua*

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P.R. China