Graphical Abstracts

Abstract

Graphical Abstract Section

Abstract

Synth. Commun. 2007, 37, 877

CONVENIENT SYNTHESIS OF 1‐ARYLMETHYL‐2‐NAPHTHOLS

Nawal K. Paul, Lindsay Dietrich, and Amitabh Jha

Department of Chemistry, Acadia University, Wolfville, NS, Canada

Abstract

Synth. Commun. 2007, 37, 889

THERMOLYSIS AND [3+2]‐CYCLOADDITION REACTIONS OF 2,3‐DIFERROCENYL‐ AND 2,3,‐DIRUTHENOCENYLCYCLOPROPENONES

Elena I. Klimova, Tatiana Klimova Berestneva, Ruben A. Toscano, Jose M. Méndez Stivalet, and Marcos Martínez Garcia

Universidad Nacional Autónoma de México, Coyoacán, México

2,3‐Diferrocenyl‐ and 2,3‐diruthenocenylcyclopropenone undergo thermolysis at ∼180°C with opening of the small ring via ketenocarbenes. Intramolecular transformation of the latter occurs with elimination of CO to yield dimetallocenylacetylenes. Alternatively, they enter into 1,3‐dipolar cycloaddition reactions with C≡C or C˭C multiple bonds to give cyclopentadienone or cyclopentenone derivatives, respectively.

Abstract

Synth. Commun. 2007, 37, 901

IMPROVED SYNTHESES OF N‐DESMETHYLCITALOPRAM AND N,N‐DIDESMETHYLCITALOPRAM

Chunyang Jin, Karl G. Boldt, Kenneth S. Rehder, and George A. Brine

Organic and Medicinal Chemistry, Science and Engineering Group, Research Triangle Institute, PO Box 12194, Research Triangle Park, USA

An improved and efficient synthesis of N‐desmethylcitalopram (2) and N,N‐didesmethylcitalopram (3) is described. The method involved N‐demethylation of citalopram (1) using 1‐chloroethyl chloroformate to give 2 in 87% yield. N,N‐Didesmethylcitalopram (3) was prepared in 57% yield from 5‐bromophthalide.

Abstract

Synth. Commun. 2007, 37, 909

PREPARATION OF A ZINC MONOCYSTEINE COMPOUND

David J. Tate Jr.¹ and David A. Newsome²

¹Tate Analytical Services, Bridge City, Louisiana, USA

²St. Luke's Cataract and Laser Institute, Tarpon Springs, Florida, USA

Both zinc and the amino acid cysteine play important roles in biological function, including antioxidant protection and tissue repair. We attempted to prepare a (1:1) zinc-cysteine complex using l‐cysteine and zinc metal. Zinc metal was added to a solution of l‐cysteine and refluxed with constant stirring. Product was selected by filtration, and after evaporation precipitation was subjected to elemental analysis, ¹H‐NMR and mass spectroscopy. The novel compound has one molecule of zinc conjugated to one molecule of cysteine.

Abstract

Synth. Commun. 2007, 37, 915

4‐SUBSTITUTED ORTHO‐(SILYLATED PHENYL)SYDNONES VIA A LITHIATION‐INDUCED SILICON MIGRATION AND SUBSEQUENT REACTION WITH ELECTROPHILES

Kenneth Turnbull and Imad F. Nashashibi

Chemistry Department, Wright State University, Dayton, Ohio, USA

Abstract

Synth. Commun. 2007, 37, 921

SOLVENT‐FREE CLAISEN CONDENSATION OF ISOPHORONE AND VERBENONE WITH PARA‐HYDROXYETHYLAMINOBENZALDEHYDES

Matthew C. Davis and Aaron J. Sathrum

Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA

A solvent-free Claisen condensation between isophorone or verbenone on two para-hydroxyethylaminobenzaldehydes is described. The method provides the condensation products quickly and, in most cases, without chromatography.

Abstract

Synth. Commun. 2007, 37, 927

SIMPLE AND EFFICIENT METHOD FOR THE SYNTHESIS OF δ‐CHLOROESTERS FROM TETRAHYDROFURAN AND ACYL CHLORIDES IN THE PRESENCE OF CATALYTIC IODINE

M. A. Pasha K. Manjula

Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India

Acyl chlorides and dry tetrahydrofuran (THF) in the presence of catalytic amounts of iodine at 25°C give δ-chloroesters in excellent yields.

Abstract

Synth. Commun. 2007, 37, 933

GREEN SYNTHESIS OF TETRAALKYLAMMONIUM TRIBROMIDE USING CERIUM(IV) AMMONIUM NITRATE (CAN) AS OXIDANT

Ruli Borah and Ashim Jyoti Thakur

Chemical Sciences Department, Tezpur University, Tezpur‐Assam, India

Abstract

Synth. Commun. 2007, 37, 941

UDCAT‐5: A NOVEL AND EFFICIENT SOLID SUPERACID CATALYST FOR CLAISEN REARRANGEMENT OF SUBSTITUTED ALLYL PHENYL ETHERS

Ganapati D. Yadav and Sharad V. Lande

Department of Chemical Engineering, University Institute of Chemical Technology (UICT), University of Mumbai, Matunga, Mumbai, India

The Claisen rearrangement of allyl phenyl ethers is a fundamental reaction in organic synthesis with a variety of applications in perfumes, flavors, pharmaceuticals, agrochemicals, polymers, fine chemicals, and intermediate industries. The development of environmentally benign processes using solid acid catalysts is becoming an area of growing interest. It was accomplished in an efficient, economical, environmentally friendly manner and was 100% selective toward alllyl phenols by employing UDCaT-5 as solid acid catalyst.

Abstract

Synth. Commun. 2007, 37, 947

SYNTHESIS OF NOVEL N‐MORPHOLINOACETYL‐2,6‐DIARYL PIPERIDIN‐4‐ONES

G. Aridoss, S. Balasubramanian, P. Parthiban, and S. Kabilan

Department of Chemistry, Annamalai University, Annamalainagar, Tamil Nadu, India

2,6-Diarylpiperidin-4-ones, upon strategical N-chloroacetylation followed by base-catalyzed condensation with morpholine, afforded an efficient route to novel N-morpholinoacetyl-2,6-diarylpiperidin-4-ones.

Abstract

Synth. Commun. 2007, 37, 959

ASYMMETRIC HYDROGENATION OF ETHYL PYRUVATE USING LAYERED DOUBLE HYDROXIDES–SUPPORTED NANO NOBLE METAL CATALYSTS

Mannepalli Lakshmi Kantam, Karasala Vijay Kumar, and Bojja Sreedhar

Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India

Enantioselective hydrogenation of ethyl pyruvate to ethyl lactate using layered double hydroxides–supported noble metal catalysts has been described.

Abstract

Synth. Commun. 2007, 37, 965

EFFICIENT APPROACH TO 4‐BENZYL‐5,5‐DIMETHYLDIHYDROFURANONES: TOTAL SYNTHESIS OF (±)‐SOLAFURANONE

A. Srikrishna, G. Satyanarayana, and Uday V. Desai

Department of Organic Chemistry, Indian Institute of Science, Bangalore, India

Abstract

Synth. Commun. 2007, 37, 977

SYNTHESIS OF SOME NOVEL 2,3,4,8,9‐PENTAHYDRO‐7‐(4‐HALOARYL)‐PYRAZOLO[5,1‐E]BENZO[1,5]OXAZOCINES AND 2,3(ERYTHRO), 7,8‐TETRA-HYDRO‐2‐ARYL‐3‐(4‐FLUORO‐3‐METHYLBENZOYL)‐6‐(4‐HALOARYL)PYRAZOLO[5,1‐D]BENZO[1,4]OXAZEPINES VIA SOLID–LIQUID PTC

Vijai N. Pathak,¹ Ragini Gupta,² Ranjana Tiwari,¹ Rekha Gupta,¹ Vineeta Sareen,¹ and Bindu Varshney¹

¹Centre for Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, India

²Department of Chemistry, Malaviya National Institute of Technology, Jaipur, India

Compounds 5 and 6 were obtained via solid–liquid PTC heterocyclization of dihydropyrazoles 4.

Abstract

Synth. Commun. 2007, 37, 985

FACILE SYNTHESIS OF 1‐ARYL‐2‐PROPANONES FROM AROMATIC AMINE

Li Li,^1,2 Hongbiao Chen,² and Yuanbin Lin²

¹School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, China

²College of Chemistry, Xiangtan University, Xiangtan, Hunan, China

A facile synthesis of aryl propanones using aromatic amines as precursors, via improved an Meerwein arylation reaction under mild conditions, is reported.

Abstract

Synth. Commun. 2007, 37, 993

ACID‐PROMOTED THIOACETALIZATION IN WATER USING 2‐(1,3‐DITHIAN‐2‐YLIDENE)MALONIC ACID AS AN ODORLESS AND EFFICIENT THIOACETALIZATION REAGENT

Yan Ouyang, Dewen Dong, Yongjiu Liang, Yanyan Chai, and Qun Liu

Department of Chemistry, Northeast Normal University, Changchun, China

Abstract

Synth. Commun. 2007, 37, 1001

SYNTHESIS OF N‐ARYL‐2‐SUBSTITUTED TETRAHYDROBENZIMIDAZOLES VIA DIRECT N‐ARYLATION

Mei‐Ying Li, He Liu, and Bo‐Hua Zhong

Department of Medicinal Chemistry, Beijing Institute of Pharmacology and Toxicology, Beijing, China

A new, simpler, and more expedient N-arylation of imidazoles was developed to synthesize a series of novel N-aryl-2-substituted tetrahydrobenzimidazoles with fair yield.

Abstract

Synth. Commun. 2007, 37, 1011

LIQUID‐PHASE SYNTHESIS OF METHYL (E)‐2‐NITROMETHYL‐2‐ALKENOATES BASED ON PEG‐SUPPORTED α‐PHENYLSELENOPROPIONATE

Shou‐Ri Sheng, Shu‐Ying Lin, Qiong Wang, Xiao‐Ling Liu, and Min Lin

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, China

An efficient procedure with operational simplicity for the liquid-phase synthesis of methyl (E)-2-nitromethyl-2-alkenoates in good yields and high purities from PEG-supported α-phenylselenopropionate is described.

Abstract

Synth. Commun. 2007, 37, 1019

PEG‐SUPPORTED SULFONIC ACID AS AN EFFICIENT AND RECYCLABLE CATALYST FOR THE SYNTHESIS OF 1,1‐DIACETATES UNDER SOLVENT‐FREE CONDITIONS

Qiu‐Ying Wang, Shou‐Ri Sheng, Mei‐Hong Wei, Zhong‐Li Xie, and Xiao‐Ling Liu

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, P. R. China

A mild, efficient and environmentally benign synthesis of 1,1‐diacetates in good yields by reaction of different aldehydes with acetic anhydride using recyclable PEG‐supported sulfonic acid as catalyst under solvent‐free conditions is reported.

Abstract

Synth. Commun. 2007, 37, 1027

ORNOCATALYTIC CONJUGATE ADDITION OF AZIDE ION TO α,β‐UNSATURATED ALDEHYDES

Sung‐Gon Kim and Tae‐Ho Park

Korea Research Institute of Chemical Technology, Daejeon, Korea

Abstract

Synth. Commun. 2007, 37, 1037

COMPARISON OF BASE‐PROMOTED AND SELF‐CATALYZED CONDITIONS IN THE SYNTHESIS OF ISOCYANATES FROM AMINES USING TRIPHOSGENE

Yiannis C. Charalambides and Stephen C. Moratti

Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, United Kingdom