Graphical Abstracts

Abstract

Synth. Commun. 2003, 33, 4005

A Convenient Method for Protection and Deprotection of Alcohols and Phenols as Alkylsilyl Ethers Catalyzed by Iodine Under Microwave Irradiation

Ira Saxena,¹ Nabajyoti Deka,¹ Jadab C. Sarma,^1,* and Sadao Tsuboi^2,*

¹Organic Chemistry Division, Regional Research Laboratory, Jorhat, Assam, India; ²Department of Environmental Chemistry and Materials, Okayama University, Okayama, Japan

Irradiation of alcohols or phenols with tert-butyldimethylsilyl chloride (TBDMSCl) or trimethylsilyl chloride (TMSCl) in presence of catalytic amount (20 mol%) of iodine in a microwave oven for 2 min gives the corresponding silyl ethers in excellent yield. Iodine in methanol deprotects the silyl ether into its parent alcohol or phenol under similar reaction conditions.

Abstract

Synth. Commun. 2003, 33, 4013

An Efficient One-Pot Synthesis of N -Methoxy- N -MethylAmides from Carboxylic Acids

Misoo Kim,^1,* Hagyoung Lee,² Ki-Jong Han,³ and Kwang-Yol Kay³

¹Department of Basic Science, and; ²Department of Chemical Engineering, Hankyong National University, Ansung, Korea; ³Department of Molecular Science and Technology, Ajou University, Suwon, Korea

Several N-methoxy-N-methylamides were prepared by the reaction of the corresponding carboxylic acids with N,O-dimethylhydroxylamine hydrochloride at room temperature using trichloromethyl chloroformate in the presence of triethylamine in excellent yields.

Abstract

Synth. Commun. 2003, 33, 4019

Synthesis of Carbamates Using Yttria-Zirconia Based Lewis Acid Catalyst

Rajesh K. Pandey,¹ Sharda P. Dagade,² Mohan K. Dongare,² and Pradeep Kumar^1,*

¹Division of Organic Chemistry: Technology, and ²Catalysis Division, National Chemical Laboratory, Pune, India

A variety of amines react with chloroformates in the presence of catalytic amount of yttria-zirconia based catalyst to afford the corresponding carbamates in excellent yields.

Abstract

Synth. Commun. 2003, 33, 4029

Acetylation of Camptothecins Using Lithium Bromide as Catalyst

N. Ravindranath, C. Ramesh, M. Ravinder Reddy, K. V. N. S. Srinivas, and Biswanath Das*

Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, India

LiBr was found to be an efficient catalyst for acetylation of promising naturally occurring anticancer alkaloids, camptothecins, containing a tertiary hydroxy group.

Abstract

Synth. Commun. 2003, 33, 4037

An Improved Iodine (III) Mediated Method for Thiocyanation of 2-Arylindan-1,3-Diones, Phenols, and Anilines

Om Prakash,^1,* Harpreet Kaur,¹ Rashmi Pundeer,¹ R. S. Dhillon,² and Shiv P. Singh¹

¹Department of Chemistry, Kurukshetra University, Kurukshetra, India; ²Department of Chemistry, Punjab Agricultural University, Ludhiana, India

An improved method for thiocyanation of 2-arylindan-1,3-diones, phenols, and anilines using a reagent combination of (dichloroiodo)benzene and potassium thiocyanate in dry dichloromethane is described.

Abstract

Synth. Commun. 2003, 33, 4043

Selective Deprotection of tert -Butyldimethylsilyl Ethers using Nafion-H®/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol

Shikha Rani, J. Lokesh Babu, and Yashwant D. Vankar*

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, India

Catalytic amounts of bromodimethyl sulfonium bromide, or Nafion-H along with NaI (1 equiv.), in methanol cleave a variety of TBDMS ethers readily in high yields. Alkyl TBDMS ethers react more readily and selectively compared to phenolic TBDMS ethers, benzyl, and methyl ethers.

Abstract

Synth. Commun. 2003, 33, 4053

A New Access to Dispiro 7-Oxaindazolidines Spiroxindole Derivatives

Rathna Durga R. S. Manian, Jayadevan Jayashankaran, and Raghavachary Raghunathan*

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

Synthesis of novel dispiroheterocyclic derivatives through 1,3-dipolar cycloaddition reaction of non-stabilized azomethine ylides with E-3-arylidene 4-chromanone and E-2-arylidene-1-tetralone has been demonstrated.

Abstract

Synth. Commun. 2003, 33, 4063

An Easy Access to Spiroisoxazoline [5,3¹] Flavan-4¹-one Through 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide to Unusual Dipolarophiles

Santhanaraman Manikandan,¹ Jayadevan Jayashankaran,² and Raghavachary Raghunathan^2,*

¹Department of Chemistry, University of North Carolina at Chapel Hill, North Carolina, USA; ²Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai, India

Synthesis of a series of novel spiro [3, 4-diaryl-4, 5-dihydroisoxazole-5,3¹-flavan-4¹-ones has been accomplished in good yields by the regioselective 1,3-dipolar cycloaddition reaction of nitrile oxide to 3-arylmethylidene flavan-4-ones.

Abstract

Synth. Commun. 2003, 33, 4071

Preparation of Novel Trialkylsilylated Propyne Derivatives from 3-Trimethylsilyl-3-ethoxycarbonylcyclopropene

Irena Zrinski and Mirjana Eckert-Maksić*

Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Zagreb, Croatia

Formation of hithertho unknown trialkylsilylated propyne derivatives 3–6 from 3-trimethylsilyl-3-ethoxycarbonylcyclopropene is described.

Abstract

Synth. Commun. 2003, 33, 4079

Synthesis of 3,3′-bi-1,2,4-Triazolo[4,5-a]benzimidazole, 5,5′-bi-1,3,4-Thiadiazole, and Thiazolo[3,2-a]benzimidazole Derivatives

Kamal M. Dawood,¹ Mohamed A. Raslan,² and Ahmad M. Farag^1,*

¹Faculty of Science, Department of Chemistry, Cairo University, Giza, Egypt

Bis-hydrazonoyl chlorides were utilized in the synthesis of the entitled heterocyclic systems.

Abstract

Synth. Commun. 2003, 33, 4087

A Simple Synthesis of Pyridine Aminophosphinic Acids and Pyridine Aminophosphine Oxides. The Unusual Cleavage of Pyridylmethyl-( N -benzylamino)-phenylphosphinic Acids and Phosphine Oxides in Acidic Solutions

Bogdan Boduszek*

Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, Wroclaw, Poland

Abstract

Synth. Commun. 2003, 33, 4095

The Synthesis of 2-Cyanomethylbenzaldehyde—Useful Substrate for Construction of Fused Ring Compounds

Andrzej Jończyk,* Marek Panasiewicz, and Tadeusz Zdrojewski

Faculty of Chemistry, Warsaw University of Technology, Warszawa, Poland

The title compound 4 has been prepared by four-step synthesis starting from methylaminoacetonitrile hydrochloride (5) and α-cyanobenzyl benzenesulfonate (6), in good yield.

Abstract

Synth. Commun. 2003, 33, 4101

Preparation of meso -Tetraarylporphyrins Nitrated in Two Neighboring Aromatic Rings

Stanisław Ostrowski^1,2,* and Beata Łopuszyńska¹

¹Institute of Chemistry, University of Podlasie, Siedlce, Poland; ²Institute of Organic Chemistry, Polish Academy of Sciences, Warszawa, Poland

Selective nitration of tetraphenylporphyrin (TPP) and its derivatives is reported. The reaction of meso-aryl substituted porphyrins with fuming yellow nitric acid (d = 1.53) at the temperature 0°C to 20°C results in the formation of 5,10-bis(4-nitroaryl)-15,20-diarylporphyrins with yields of 30–83%.

Abstract

Synth. Commun. 2003, 33, 4111

Synthesis of Selectively Protected Genistein Derivatives

Wiesław Szeja,¹ Gabriela Pastuch,¹ Ilona Wandzik,^1,* Nikodem Kuźnik,¹ and Grzegorz Grynkiewicz²

¹Faculty of Chemistry, Silesian University of Technology, Gliwice, Poland; ²Pharmaceutical Research Institute, Warszawa, Poland

Differential functionalization of the phenolic groups in genistein by sequential silylation/acylation reactions, involving some unexpected regioselective O-silyl group replacement, is described.

Abstract

Synth. Commun. 2003, 33, 4123

A Facile Method for the Synthesis of Dihydrofuranonaphthoquinones, Furanonaphthoquinones, and Benzofuranonaphthoquinones

Yong Rok Lee* and Byung So Kim

School of Chemical Engineering and Technology, College of Engineering, Yeungnam University, Kyongsan, Korea

An efficient synthesis of dihydrofuranonaphthoquinone, furanonaphthoquinone, and benzonaphthoquinone derivatives has been carried out starting from 2-hydroxy-1,4-naphthoquinone and a variety of vinyl sulfides in moderate yields.

Abstract

Synth. Commun. 2003, 33, 4137

An Efficient Deoxygenation of Heteroaromatic N -Oxides Using Zinc Dust/Ammonium Formate Reagent System

Roman Balicki,* Marcin Cybulski, and Grzegorz Maciejewski

Pharmaceutical Research Institute, Warsaw, Poland

Heteroaromatic N-oxides were readily and selectively deoxygenated to the corresponding bases with zinc/ammonium formate reagent system.

Abstract

Synth. Commun. 2003, 33, 4143

An Effective Approach for the Silylation of Hydroxyl Compounds in Room Temperature Ionic Liquids

Zhen-Yuan Xu,* Dan-Qian Xu, Bao-You Liu, and Shu-Ping Luo

Catalytic Hydrogenation Research Centre, Zhejiang University of Technology, Hangzhou, Zhejiang, China

The room temperature ionic liquid (RTIL) 1-n-butyl-3-methylimidazolium hexafluorophosphate (BMImPF₆) is used as a “green” recyclable alternative to conventional solvents for the silylation of a series of hydroxyl compounds (alcohols and phenols) with t-butyldimethylchlorosilane (TBDMCS), which has some advantages such as simplicity of the synthetic procedure, the potential for recycling of the ionic liquid and the environmentally benign.

Abstract

Synth. Commun. 2003, 33, 4151

Diastereoselective Addition of Organozinc Reagents to Benzaldiminetricarbonylchromium Derivatives

Kaori Ishimaru,* Kyoko Ohe, Emi Shindo, and Takakazu Kojima

Department of Chemistry, The National Defense Academy, Hashirimizu, Yokosuka, Japan

Diastereoselective addition of organozinc reagents to benzaldiminetricarbonylchromium derivatives was carried out by using Lewis acid to give the corresponding amines.

Abstract

Synth. Commun. 2003, 33, 4157

A Convenient Route to Symmetric Phosphate, Phosphorothioate, and Phosphoroselenoate of AZT and D4T

Qiang Xiao, Yong Ju,* and YuFen Zhao*

The Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing, China

The symmetric phosphate, phosphonothioate and phosphonoselenoate derivatives of AZT and D4T were synthesized in an expeditious way and high yields. The structures of these compounds were confirmed by the NMR and ESI-MS methods.

Abstract

Synth. Commun. 2003, 33, 4163

The Preparation of 5-Aryl 5-methyl-4,5-dihydroisoxazoles from Dilithiated C(α),O-Oximes and Select Acetyl Ketones

Matthew J. Walters, S. Patrick Dunn, Emily Choi, Amanda N. D′Elia, Morgan E. Warner, and Charles F. Beam*

Department of Chemistry and Biochemistry, College of Charleston, Charleston, South Carolina, USA

Several 5-aryl-5-methyl-4,5-dihydroisoxazoles were prepared by a three-step, one-pot process in 24–83% yield. C(α),O-oximes were dilithiated with lithium diisopropylamide and condensed with electron enriched acetophenones, such as 4′-methoxyacetophenone, followed by immediate acid cyclization.

Abstract

Synth. Commun. 2003, 33, 4173

A New Preparation of gem-bis(difluoramino)alkanes via Direct Fluorination of Geminal Bisacetamides

Robert D. Chapman,^1,* Matthew C. Davis,¹ and Richard Gilardi²

¹Research Department (Code 4T4200D), Naval Air Warfare Center Weapons Division, Naval Air Systems Command, China Lake, California, USA; ²Laboratory for the Structure of Matter (Code 6030), Naval Research Laboratory, Washington, DC, USA

A fundamentally new preparation of internal and terminal gem-bis(difluoramino)alkanes has been demonstrated by the direct fluorination of corresponding gem-bisacetamides, specifically, 1,1-bisacetamidocyclohexane and 1,1-bisacetamidopropane, leading to 1,1-bis(difluoramino)cyclohexane, and 1,1-bis(difluoramino)propane, respectively.