Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 409

Michael Addition Catalyzed by Potassium Hydroxide under ultrasound

Ji-Tai Li,* Yong Cui, Guo-Feng Chen, Zhao-Li Cheng, and Tong-Shuang Li

College of Chemistry and Environmental Science, Hebei University, Baoding, P.R. China

Michael addition of chalcone with active methylene compounds catalyzed by potassium hydroxide results Michael adducts in 75–98% yield under ultrasound irradiation.

Abstract

Synth. Commun. 2003, 33, 403

Application of Amberlite IRA-400 (Basic) as a Base in Heck Reaction

S. B. Solabannavar, V. B. Helavi, U. V. Desai, and R. B. Mane*

Department of Chemistry, Shivaji University, Kolhapur 416004, India

Amberlite IRA-400 (basic) has been used as a base in the Heck reaction and the generated quarternary ammonium salt might also be assisting in the reaction. The reaction is clean, simple and yields are high. The resin can be regenerated, recycled and the work-up procedure becomes simple compared to other bases used.

Abstract

Synth. Commun. 2003, 33, 393

A Facile and Efficient Synthesis of Ultraviolet Absorber 3-Dihexylaminoallylidenemalononitrile

Ya-Fei Ji,* Zhi-Min Zong, and Xian-Yong Wei*

School of Chemistry Engineering, China University of Mining and Technology, Xuzhou 221008, Jiangsu, P.R. China

Synthesis of 1 via addition–oxidation of propinol with dihexylamine to give 2, and condensation with malononitrile in an overall yield of 73.3%.

Abstract

Synth. Commun. 2003, 33, 387

Synthesis of 25,26,27- tris (Ethoxycarbonylmethoxy)-28-(substituted oxy-carbonylmethoxy) Calix-4-arene: First Example of Calix-imidazole/Benzimidazole Analog

Pratibha Sharma,* Ashok Kumar, and Anupam Mandloi

Institute of Chemical Sciences, Devi Ahilya University, Indore 452017, M.P., India

Synthesis of calix-imidazole/benzimidazole analog i.e., 25,26,27-tris(ethoxycarbonylmethoxy)-28- ({2′-phenylcarbamoyl} benzimidazolyloxycarbonylmethoxy) calix-4-arene 6 _a–c .

Abstract

Synth. Commun. 2003, 33, 381

A Convenient Synthesis of Conjugated ω-Arylpolyenals via Wittig Reaction with (1,3-Dioxan-2-yl-methyl)Triphenylphosphonium Bromide/Sodium Hydride

Damian Plażuk, Izabela Janowska, Arkadiusz Kłys, Asia Hameed, and Janusz Zakrzewski*

Department of Organic Chemistry, University of Łódź, Łódź, Narutowicza 68 Poland

(1,3-Dioxan-2-yl-methyl)triphenylphosphonium bromide, sodium hydride and a catalytic amount of 18-crown-6 has proven efficient system for vinylic extension of ω-arylpolyenals.

Abstract

Synth. Commun. 2003, 33, 373

Synthesis of Some Novel γ-Spiroiminolactones from Reaction of Cyclohexyl Isocyanide and Dialkyl Acetylene Dicarboxylates with 1-Benzylisatin and Tryptanthrine

Javad Azizian,* Ali R. Karimi, and Ali A. Mohammadi

Department of Chemistry, Faculty of Science, Shahid Beheshti University, P.O. Box 19395-4716, Tehran, Iran

1:1 intermediate generated by the addition of cyclohexyl isocyanide to dialkyl acetylenedicarboxylates, undergoes facil addition to 1-benzylisatin and tryptantrin to afford highly functionalized novel unsaturated γ-spiroiminolactones in moderate to high yields.

Abstract

Synth. Commun. 2003, 33, 367

Tandem Michael-Wittig-Horner Reaction: Application to the Synthesis of Bisabolanes

Olivier Chuzel and Olivier Piva*

Laboratoire de Chimie Organique, Photochimie et Synthèse, UMR 5622, Université Claude Bernard, Lyon I, France

Abstract

Synth. Commun. 2003, 33, 507

Polyethylene Glycol Supported Chloro[1,3,5]triazine: A Novel Synthetic Auxiliary for the Liquid-phase Synthesis of Alkynyl Benzamide Derivatives

Min Xia and Yanguang Wang*

Department of Chemistry, Zhejiang University, Hangzhou, 310027, P.R. China

2,4,6-Trichloro[1,3,5]triazine was loaded on polyethylene glycol 4000 to give a new supported reagent which was employed to carry out the liquid-phase Sonogashira coupling reaction, offering alkynyl benzamide derivatives in high yields under mild conditions by cleavage with amines.

Abstract

Synth. Commun. 2003, 33, 499

Direct and Improved Access to Unsymmetrically Functionalized Bipyridines by a Stille-Type Cross-Coupling Reaction

Julien Mathieu and Alain Marsura*

Groupe d'Etude des Vecteurs Supramoléculaires du Médicament, UMR CNRS-UHP 7565, Université Henri Poincaré-Nancy I, 5 rue A. Lebrun, BP 403, 54001 Nancy, France

The Stille-type cross-coupling reaction on mesylate, tosylate and triflate allowed synthesis of symmetrical and unsymmetrical monofunctionalized 2′2′-bipyridines in possible multigram scales.

Abstract

Synth. Commun. 2003, 33, 493

An Efficient One-Pot Procedure for Preparation of 2,4(1 H ,3 H )-Quinazolinediones and 2-Thioxoquinazolinone Derivatives Under Microwave Irradiation

Javad Azizian,* Ali A. Mohammadi, and Ali R. Karimi

Department of Chemistry, Faculty of Science, Shahid Beheshti University, P.O. Box 19395-4716, Tehran, Iran

An efficient one-pot synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinone derivatives are given by the condensation of isatoic anhydride, primary amine and urea or thiourea in the absence of organic or inorganic reagents under microwave irradiation.

Abstract

Synth. Commun. 2003, 33, 361

A High Regioselective Synthesis of Novel Dispiro[oxindole-cyclohexanone]pyrrolidines

Ambrose Amal Raj and Raghavachary Raghunathan*

Department of Organic Chemistry, University of Madras, A. C. College Campus, Chennai 25, Tamil Nadu, India

Abstract

Synth. Commun. 2003, 33, 481

An Improved Synthesis of ( E )-Cinnamic Acid Derivatives via the Claisen-Schmidt Condensation

Masanori Hatsuda, Tooru Kuroda, and Masahiko Seki*

Product & Technology Development Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532-8505, Japan

A variety of (E )-cinnamic acid derivatives are prepared in high yields through a condensation of aldehydes with methyl acetate in the presence of sodium metal and a catalytic amount of methanol in toluene.

Abstract

Synth. Commun. 2003, 33, 475

Enantioselective Epoxidation of α,β-Unsaturated Ketones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts

Dae Young Kim,^1,* Young Jae Choi,¹ Hai Yoon Park,¹ Chang Ung Joung,¹ Kwang Oh Koh,¹ Joo Yang Mang,¹ and Kang-Yeoun Jung²

¹Department of Chemistry, Soonchunhyang University, Asan P.O. Box 97, Chungnam 336-600, Korea

²Department of Industrial Chemistry, Kangnung National University, Kangnung, Korea

Treatment chalcone derivatives with sodium hypochlorite under mild reaction conditions afforded the corresponding epoxy ketones in good yields with good to moderate enantiomeric excesses.

Abstract

Synth. Commun. 2003, 33, 463

A New Protocol for Selective Deprotection of N - tert -Butoxycarbonyl Protective Group ( t -Boc) with Sn(OTf)₂

D. Subhas Bose*, K. Kiran Kumar, and A. V. Narsimha Reddy

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

A mild and efficient method for the selective removal of t-Boc group from the corresponding nitrogen derivativers is described which utilizes tin(II)trifluoromethanesulfonate as reagent of choice in high yields.

Abstract

Synth. Commun. 2003, 33, 457

Microwave-Promoted N -Alkylation of Acridones Without Solvent

Cunde Wang,* Tianlong Hang, and Hui Zhang

Department of Chemistry, Yangzhou University, Yangzhou 225002, P.R. China

N-Alkylacridones (3) were effectively synthesized in few minutes by a reaction of acridone and alkyl halides with NaOH/K₂CO₃ absorbed on Al₂O₃ in the presence of TBAB under microwave irradiation without solvent.

Abstract

Synth. Commun. 2003, 33, 451

Rapid Removal of Benzyloxycarbonyl Groups from 1,4,7,10-Tetraazacyclododecane Derivatives by Catalytic Transfer Hydrogenation

Charles H. Manning, Anna Skwierawska, John N. Marx, and Darryl J. Bornhop*

Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA

We report that N-benzyloxycarbonyl groups can be conveniently removed from 1,4,7,10-tetraazacyclododecanes by catalytic transfer hydrogenation with cyclohexene and 5% palladium–carbon catalyst. The process is rapid, selective, inexpensive, and is high yielding.

Abstract

Synth. Commun. 2003, 33, 445

Synthesis of Benzomacrolactam by 12- endo Selective Aryl Radical Cyclization of N -(4-Allyloxybutyl)-2-iodobenzamide

André Augusto Gomes Faraco,¹ Maria Auxiliadôra F. Prado,^2,* Ricardo J. Alves,² José D. Souza Filho,¹ Rosemeire Brondi Alves,¹ and Renata F. Prado Faraco²

¹Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Antônio Carlos 6627, Belo Horizonte 31270-200, Brasil

²Departamento do Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Avenida Olegário Maciel 2360, Belo Horizonte 30180-112, Brasil

Regioselective 12-endo aryl radical cyclization of N-(4-allyloxybutyl)-2-iodobenzamide (7) with tri-n-butyltin hydride provided benzomacrolactam 15. The structure of 15 is supported by ¹H and ¹³C NMR spectroscopy and by DEPT, COSY, COSYLR and HMQC experiments.

Abstract

Synth. Commun. 2003, 33, 435

Microwave Assisted Improved Synthesis of 6-Formylpterin and Other Heterocyclic Mono- and Di-Aldehydes

Shyamaprosad Goswami* and Avijit Kumar Adak

Department of Chemistry, Bengal Engineering College (Deemed University), Howrah 711 103, West Bengal, India

A series heterocyclic mono- and di-aldehydes has been synthesized by selerium dioxide under microwave conditions.

Abstract

Synth. Commun. 2003, 33, 427

A Modified Procedure for the Preparation of Linear Polymines

Amparo Sánchez-Sandoval,¹ Cecilio Álvarez-Toledano,² René Gutiérrez-Pérez,³ and Yasmi Reyes-Ortega^1,*

¹Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, 14 Sur 6301, Col. San Manuel, Puebla, Pue. 72570, México

²Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, México, D. F. 04510, México

³Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, P.O. Box 1067, Puebla, Pue. 72001, México

An efficient method has been developed for obtaining linear polydentate free amines with high purity and yield than the route currently available.

Abstract

Synth. Commun. 2003, 33, 421

A Rapid and Facile Preparation of Methyl 4,6- O -Benzylidene-α-d-Glucopyranoside and Some Related Compounds

Cosam C. Joseph,* Binne Zwanenburg, and Gordon J. F. Chittenden^†

Department of Organic Chemistry, NSR Center, University of Nijmegen, Toernooiveld, 6525 ED Nijmegen, The Netherlands

A simple and rapid benzylidenation procedure for preparing the title compound and other related derivatives using tin(II) triflate and other triflate salts as catalysts is described.

Abstract

Synth. Commun. 2003, 33, 415

A Novel Entry into a New Class of Dispiroheterocycles Through Azomethine Ylides Involving Unusual Dipolarophiles

Jayadevan Jayashankaran, S. Manikandan, and R. Raghunathan*

Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 25, India

Synthesis of novel dispiroheterocyclic derivatives through 1,3-dipolar cycloaddition reaction of azomethine ylides with 3-arylidene croman-4-one has been demonstrasted.

Abstract

Synth. Commun. 2003, 33, 353

An Efficient and Practical Synthesis of N , N -Diethyl-7-Indolyloxyacetamide via 7-Hydroxyindole

Hiroshi Harada,* Akihito Fujii, and Shiro Kato

Medicinal Chemistry Group, Chemistry Research Laboratories, Dainippon Pharmaceutical Co., Ltd., Enoki 33-94, Suita, Osaka 564-0053, Japan

An efficient and practical synthesis of N,N-diethyl-7-indolyloxyacetamide from 3-hydroxy-2-nitrotoluene via 7-hydroxyindole is reported.