Graphical Abstracts

Abstract

Graphical Abstract Section

Abstract

Synth. Commun. 2006, 36, 835

FACILE ONE‐POT SYNTHESIS OF 3,4‐DIHYDROPYRIMIDIN‐2(1H)‐ONE CATALYZED BY Zn(NH₂SO₃)₂

Min Zhang and Yi‐Qun Li

Department of Chemistry, Jinan University, Guangzhou, China

An efficient synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones (DHPMS) from aromatic aldehydes, β‐keto ester, and urea (or thiourea) in refluxing ethanol using zinc sulfamate as a catalyst is described. Compared to the classical Biginelli reaction, this new method consistently has the advantages of good yields (76%–96%), short reaction time (2–5 h), no corrosion of equipment, ease of manipulation, and low‐cost catalyst.

Abstract

Synth. Commun. 2006, 36, 843

EXPEDITIOUS ONE‐STEP METHOD TO 5‐ARYL‐2‐FUROYL SUBSTITUTED THIOUREAS AND THIOSEMICARBAZIDES IN AQUEOUS MEDIA

Xicun Wang, Zhang Zhang, Zhengjun Quan, Mangang Wang, Fang Wang, and Zheng Li

GanSu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, China

An expeditious and green approach to 5‐aryl‐2‐furoyl substituted thioureas and thiosemicarbazides in aqueous media via one‐step procedure.

Abstract

Synth. Commun. 2006, 36, 849

CHEMOSELECTIVE ADDITION OF HYDRAZINE TO δ‐KETO ESTERS AND DIMETHYLFORMAMIDE‐MEDIATED DEESTERIFICATION

Sivaperuman Saravanan, Vellaisamy Sridharan, and Shanmugam Muthusubramanian

Department of Organic Chemistry, Madurai Kamaraj University, Madurai, India

The chemoselective reaction of hydrazine on ketone rather than the ester in a gem diester system with a γ‐keto group by hydrazinium sulfate and a tandem deesterification of one of the esters in this system by N,N‐dimethylformamide are reported.

Abstract

Synth. Commun. 2006, 36, 859

NOVEL AND GRAM‐SCALE GREEN SYNTHESIS OF FLUTAMIDE

B. P. Bandgar and S. S. Sawant

Organic Chemistry Research Laboratory, School of Chemical Sciences, S. R. T. M. U., Nanded, India

Isobutyric acid in the presence of cyanuric chloride and N‐methylmorpholine was converted into active ester 3 at 0–5 °C, and it was subsequently treated with 3‐aminobenzotrifluoride 4 at 25 °C to furnish corresponding amide 5. This amide finally, on nitration, produced the desired product flutamide, 2‐methyl‐N‐[4‐nitro‐3‐(trifluoromethyl)phenyl]propionamide 6, in good yield. By‐product 2,4,6‐trihydroxy‐1,3,5‐triazine 7 was converted into the useful starting material cyanuric chloride 1 by refluxing with N,N‐diethylamine and POCl₃.

Abstract

Synth. Commun. 2006, 36, 865

SYNTHESIS OF BETAMETHASONE FROM THE WASTE OF THAI AGAVE SISALANA

Ngampong Kongkathip, Boonsong Kongkathip, and Naratitt Noimai

Natural Products and Organic Synthesis Research Unit (NPOS), Department of Chemistry, Faculty of Science, Kasetsart University, Chatuchak, Bangkok, Thailand

Betamethasone was synthesized from hecogenin, which was obtained from the waste of Thai Agave sisalana.

Abstract

Synth. Commun. 2006, 36, 875

HYPERVALENT IODINE IN THE SYNTHESIS OF BRIDGEHEAD HETEROCYCLES: A FACILE ROUTE TO THE SYNTHESIS OF 6‐ARYLIMIDAZO[2,1‐B]THIAZOLES USING [HYDROXY(TOSYLOXY)IODO]BENZENE

Ranjana Aggarwal and Garima Sumran

Chemistry Department, Kurukshetra University, Kurukshetra, Haryana, India

α‐Tosyloxyketones (2), readily accessible through hypervalent iodine oxidation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene (HTIB) in acetonitrile, exclusively generates the 6‐arylimidazo[2,1‐b]thiazoles (4) on treatment with commercially available 2‐aminothiazole (3).

Abstract

Synth. Commun. 2006, 36, 881

MICROWAVE‐ASSISTED FACILE SYNTHESIS AND CRYSTAL STRUCTURE OF CIS‐9,10,11,15‐TETRAHYDRO‐9,10[3′,4′]‐FURANOANTHRACENE‐12,14‐DIONE

Weerachai Phutdhawong,¹ Duang Buddhasukh,² Stephen G. Pyne,³ Apinpus Rujiwatra,² and Chaveng Pakawatchai⁴

¹Department of Chemistry, Maejo University, Chiang Mai, Thailand ²Department of Chemistry, Chiang Mai University, Chiang Mai, Thailand ³Department of Chemistry, University of Wollongong, Wollongong, Australia ⁴Department of Chemistry, Prince of Songkla University, Hat Yai, Songkhla, Thailand

Abstract

Synth. Commun. 2006, 36, 885

CONJUGATE ADDITION OF A SILYL KETENE ACETAL TO α,β‐UNSATURATED LACTONES

Rudhramyna Gnaneshwar and Swaminathan Sivaram

Division of Polymer Science and Engineering, National Chemical Laboratory, Pune, India

Abstract

Synth. Commun. 2006, 36, 891

SYNTHESIS OF [¹²⁵I]‐, [²H]‐, AND [³H]‐LABELED 3‐IODOTHYRONAMINE (T₁AM)

Motonori Miyakawa and Thomas S. Scanlan

Departments of Pharmaceutical Chemistry and Cellular and Molecular Pharmacology, University of California at San Francisco, San Francisco, California

Synthesis of [¹²⁵I]‐, [²H]‐, and [³H]‐T₁AM is described, employing readily available materials and simple reaction conditions.

Abstract

Synth. Commun. 2006, 36, 903

SYNTHESIS OF 7,8‐DIHYDROTHIENO[3′,2′:4,5]PYRROLO[1,2‐A]PYRAZIN‐5(6H)‐ONES USING A MODIFICATION OF FOUR‐COMPONENT UGI REACTION

Alexey P. Ilyin,¹ Vladimir V. Kobak,² Irina G. Dmitrieva,² Yulia N. Peregudova,² Veronika A. Kustova,² Yulia S. Mishunina,² Sergey E. Tkachenko,^1,2 and Alexandre V. Ivachtchenko¹

¹ChemDiv, Inc., San Diego, California, USA

²Department of Organic Chemistry, Chemical Diversity Research Institute, Moscow, Russia

Abstract

Synth. Commun. 2006, 36, 911

SYNTHESIS AND CHEMICAL TRANSFORMATIONS OF 6‐(MORPHOLINE‐4‐SULFONYL)‐QUINOLINE‐2,3,4‐TRICARBOXYLIC ACID

Dmitri V. Kravchenko,¹ Volodymyr M. Kysil,² Alexey P. Ilyn,¹ Sergey E. Tkachenko,^1,2 Sergey Maliarchouk,^1,2 Ilya M. Okun,^1,2 and Alexandre V. Ivachtchenko²

¹Chemical Diversity Research Institute, Khimki, Moscow, Russia

²ChemDiv, Inc., San Diego, CA, USA

Abstract

Synth. Commun. 2006, 36, 919

STEREOSPECIFIC SYNTHESIS OF (2E,13Z)‐2,13‐OCTADECADIENYL ACETATE, THE SEX PHEROMONE COMPONENT OF THE LEPIDOPTERA SPECIES

Jacek Grodner

Institute of Industrial Organic Chemistry, Warsaw, Poland

A concise synthesis of (2E‐13Z)‐2,13‐octadecadienyl acetate from 12‐(2‐tetrahydropyranyloxy)‐1‐dodecyne is described.

Abstract

Synth. Commun. 2006, 36, 925

MORE EFFICIENT PALLADIUM CATALYST FOR HYDROGENOLYSIS OF BENZYL GROUPS

Yong Li,¹ Govindaswamy Manickam,² Atanu Ghoshal,² and Prasad Subramaniam²

¹Kosan Biosciences Inc., Hayward, California, USA

²Syngene International Pvt. Ltd., Bangalore, India

Abstract

Synth. Commun. 2006, 36, 929

TANDEM FAVORSKII INTERMEDIATE/CYCLIZATION LEADING TO TRICYCLO[4.4.0.0]DECANEDIONES

Sasan Karimi,¹ Julia Christodoulou,² and Gopal Subramaniam²

¹Department of Chemistry, Queensborough Community College/CUNY, Bayside, New York, USA

²Department of Chemistry and Biochemistry, Queens College/CUNY, Flushing, New York, USA

Abstract

Synth. Commun. 2006, 36, 935

REGIOSELECTIVE ENDOCYCLIC OXIDATION OF ENANTIOPURE 3‐ALKYLPIPERIDINES: SYNTHESIS OF (3S,5S)‐(‐)‐3‐ETHYL‐5‐METHYLPIPERIDINE

Alejandro Castro, Jorge Juárez, Dino Gnecco, Joel L. Terán, Laura Orea, and Sylvain Bernès

Centro de Química, Instituto de Ciencias, BUAP, Puebla, México

An efficient regioselective endocyclic oxidation of enantiopure 3‐alkylpiperidines 1(a–c) with bromine in acetic acid to generate as main products the corresponding 5‐alkylpiperidin‐2‐ones 3(a–c) is described. In addition, starting from 3a or 3b, the synthesis of (3S,5S)‐(‐)‐3‐ethyl‐5‐methylpiperidine 6·HCl was achieved.

Abstract

Synth. Commun. 2006, 36, 943

THALLIUM(III) NITRATE MEDIATED RING CONTRACTION OF 2‐ARYL‐1,2,3,4‐TETRAHYDRO‐4‐QUINOLONES: STEREOSELECTIVE SYNTHESIS OF TRANS METHYL 2‐ARYL‐2,3‐DIHYDROINDOL‐3‐CARBOXYLATES

Om V. Singh, M. Muthukrishnan, and M. Sundaravedivelu

Phytochemistry Division, Tropical Botanic Garden and Research Institute, Pacha Palode, Trivandrum, India

Abstract

Synth. Commun. 2006, 36, 951

NEW 1,4‐DIARYL [1,2,3]‐TRIAZOLE LIQUID CRYSTALS USING A CLICK REACTION

Gilmar Conte,¹ Rodrigo Cristiano,¹ Fernando Ely,² and Hugo Gallardo¹

¹Departamento de Química, Universidadade Federal de Santa Catarina, Campus Trindade, Florianópolis, Brazil

²Divisão de Mostradores de Informação, Centro de Pesquisas Renato Archer, Campinas, Brazil

Abstract

Synth. Commun. 2006, 36, 959

RAPID, ACID‐MEDIATED DEPROTECTION OF SILYL ETHERS USING MICROWAVE HEATING

R. David Crouch and Anna B. Williams

Department of Chemistry, Dickinson College, Carlisle, Pennsylvania, USA

Microwave heating of TES‐ and TBS‐protected 1° and 2° alcohols in a mixture of equal parts acetic acid, THF, and water allows deprotection in as little as 5 min. TBDPS‐ and TIPS‐protected alcohols and silyl‐protected phenols are stable in these conditions. Thus, selective deprotection of more labile silyl ethers in the presence of TIPS‐ or TBDPS‐protected alcohols is possible. Similarly, alkyl silyl ethers can be deprotected in the presence of aryl silyl ethers.

Abstract

Synth. Commun. 2006, 36, 965

SYNTHESIS OF 7,6‐FUSED BICYCLIC LACTAMS FOR USE AS BETA‐TURN MIMICS

Omar Morales, Wesley Seide, and Samuel E. Watson

Department of Chemistry and Biochemistry, Long Island University, Brooklyn, New York, USA

An improved synthesis of (3S, 7R, 11S) methyl 2‐oxo‐3‐N‐phthyaloyamino‐1‐azabicyclo[5.4.0]undecane‐11‐carboxylate from (S)‐2‐aminohexanoic acid and (S)‐allylglycine is presented.

Abstract

Synth. Commun. 2006, 36, 975

SYNTHESIS OF [RING‐³H] DOPAMINE AND FLUORO ANALOGUES AT HIGH SPECIFIC ACTIVITY

Crist N. Filer, Demetri Orphanos, and Richard J. Seguin

PerkinElmer Life and Analytical Sciences Inc., Boston, Massachusetts, USA

Dopamine and several fluoro analogues were labeled with tritium at high specific activity by a catalytic tritium dehalogenation of polybromo precursors.

Abstract

Synth. Commun. 2006, 36, 979

SYNTHESIS OF NOVEL FERROCENYL OXINDOLE AND FERROCENE SUBSTITUTED DISPIROHETEROCYCLES THROUGH [3+2]CYCLOADDITION OF AZOMETHINE YLIDES

J. Jayashankaran, Rathna Durga, R. S. Manian, and R. Raghunathan

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