Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

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VOLUME 44 B

                                   NUMBER 7

JULY 2005

CONTENTS

Rapid Communications

 

 

 

1427

Zinc mediated facile and efficient dehydration of aldoximes to nitriles

 

IPC: Int.Cl.7 C 01 G 9/00, C 07 C 251/32, C 07 D 213/57, C07 D 307/08

 

An efficient method of dehydration of aldoximes to nitriles induced by zinc-iodine system in excellent yields at room temperature is described.

 

 

 

Anil Saini, Sanjay Kumar & Jagir S Sandhu*

 

 

 

 

Papers

 

 

 

1430

Enantiospecific synthesis of B-seco-nortaxanes from two molecules of carvone

 

IPC: Int.Cl.7 C 07 C

 

Enantiospecific synthesis of a B-seco-nortaxane has been accomplished starting from two molecules of (R)-carvone.

 

 

A Srikrishna*, P Praveen Kumar &

T Jagadeeswar Reddy

 

 

 

 

 

 

 

 

1437

Synthesis of 2-(amino acid ester)-6-(1,1-dimethyl­ethyl)-3-cyclohexyl-2H-3,4-dihydro-1,3,2-benzo­xa­za­phospho­rin 2-sulfides/oxides

 

IPC: Int.Cl.7 C 07 D

The title compounds 4a-j are accomplished through a two step process. It involves the prior preparation of the monochloride as 2-chloro-6-(1,1-dimethylethyl)-3-cyclohexyl-2H-3,4-dihydro-1,3,2-benzoxaza­phos­pho­rin 2-sulfide/ oxide 3a/3b and their subsequent reaction with the amino acid methyl ester hydrochlorides 1a-e in dry tetrahydrofuran in the presence of triethylamine at various temperatures.

 

 

P Vasu Govardhana Reddy, P Haranath,

C Suresh Reddy*  & C Naga Raju

 

 

 

 

 

 

 

 

 

 

 

1441

Synthesis of 4-(benzamide)- and 4-(phthalimide)-substituted phenoxypropanolamines and their b1-, b2-adrenergic receptor binding studies

 

IPC: Int.Cl.7 C 07 D

Synthesis and b1-, b2-adrenergic receptor binding of 4-(benzamide)- and 4-(phthalimide)-substituted phenoxy­propanolamines are reported. Many of the compounds show selective affinity to b1-adrenergic receptor.   

 

 

 

 

 

 

Dharam Paul Jindal, Babita Singh,

Mohane Selvaraj Coumar* , Giancarlo Bruni &

Paula Massarelli

 

 

 

 

 

 

 

1446

Synthesis of novel angularly fused pentacyclic heterocycles of pharmacological interest

 

IPC: Int.Cl.7 C 07 D // A 61 P 31/04, 3110, 25/08, 33/10, 29/00

2-Substituted-tetrazolo[1,5-c]pyrimido[5,4-b]naph­tho­­[2,1-b]furans, triazolo[4,3-c]pyrimido[5,4-b]naphtho­[2,1-b]furans and 4-arylidinehydrazinonaphtho[2,1-b]furo[3,2-d]pyrimidines derivatives have been pre­pared from 2-substituted-4-hydrazinonaphtho[2,1-b]furo[3,2-d]pyrimidines by reacting with appropriate reagents. The newly synthesized compounds have been screened for antimicrobial, anthelmintic, anti­convulsant and antipyretic activities.

 

 

 

 

 

 

Basavaraj Padmashali, V P Vaidya*,

K M Mahadevan & K P Latha

 

 

 

 

 

 

 

 

 

1452

Synthesis of pyrazole imines and azetidinone compounds using conventional and microwave technique and studies of their antibacterial activity

 

IPC: Int.Cl.7 C 07 D 277/02

2-Azetidinones 4 have been prepared by the reaction of Schiff bases 3 with chloroacetyl chloride and triethylamine. The reaction is carried out by conventional and microwave method. 

 

 

Ketan Mistry* & K R Desai

 

 

 

 

 

 

 

1456

Synthesis of 1,3,4-oxadiazoles carrying imidazole moiety

 

IPC: Int.Cl.7 C 07 D 233/00, 27/10 // A 61 P 31/04, 31/10

A new series of 1,3,4-oxadiazoline derivatives 5a-l have been obtained by cyclisation of various hydrazones 4 with acetic anhydride. The hydrazones 4 in turn are obtained by the reaction of appropriate carbonyl compound with 2-methyl-5-nitro-imidazole-1-acethydrazide 3. The new products are characteri­zed by spectral and analytical data. Most of the tested compounds show promising antibacterial and antifungal activity.

 

 

Priya V Frank & Balakrishna Kalluraya*

 

 

 

 

 

 

 

1460

Synthesis of potential fungicidal bibenzyls from bio-renewable source

 

IPC: Int.Cl.7 C 07 C 15/00 // A 61 P

Microwave assisted expeditious synthesis of 4,4'-bis(3"-aryl-2"-methyl -5"-methyl/ carboxymethyl-4"-oxo-thiazolidin-2"-yl)bibenzyls 3a-n with excellent yield (88-94%) is reported. The rate of the reaction is enhanced 225 times in comparison with conventional method. Antifungal screening results on Fusarium oxysporum and Penicillium citrinum show that most of the synthesized compounds display promising antifungal activity.

 

 

Ibadur R Siddiqui*, Jaya Singh, Pravin K Singh & Jagdamba Singh

 

 

 

 

 

 

 

 

 

1465

Synthesis and screening of 1,3,4-oxadiazino­indo­li­none and s-triazole derivatives of pyranobenzo­pyran

 

IPC: Int.Cl.7 C 07 D 311/76

A facile synthesis and screening of 1,3,4-oxa­di­azinoindolinone and s-triazole derivatives of pyrano­benzopyran

 

 

 

 

V V Mulwad*, A C Chaskar & J M Shirodkar

 

 

 

 

 

 

 

1470

Chemoselective reaction of benz(g)indole based bisheterocycle dicarboxylate towards hydrazine hydrate: Synthesis and antimicrobial activity of new triheterocycles-5-pyrrolylaminocarbonyl/ mer­ca­ptooxadiazolyl/4-allyl-5-mercaptotriazolyl­methoxy-1-furfuryl-2-methylbenz(g)indoles

 

IPC: Int.Cl.7 C 07 D 209/60 // A 61 P 31/04, 31/10

 

 

 

Dundappa S Donawade, A V Raghu,

U M Muddapur & Guru S Gadaginamath*

 

 

 

 

 

 

 

 

 

 

 

 

1476

‘Huisgen reaction’ of aldonitrones with N-benzyl maleimide leading to synthesis of 2, 3-diaryl-5-benzyl-2H-3, 3a, 4, 5, 6, 6a-hexahydropyrrolo[3, 4-d]isoxazole-4, 6-diones

 

IPC: Int.Cl.7 C 07 D

1,3-Dipolar cycloaddition reaction of variously substituted aldonitrones with N-benzyl maleimide leads to synthesis of substituted 2, 3-diaryl-5-benzyl-2H-3, 3a,4,5,6,6a-hexahydropyrrolo[3, 4-d]isoxazole-4,6-diones in good yield. Structures and stereo­chemistry of the products have been determined by spectral studies.

 

 

 

 

 

 

Jaspreet Kaur*, Baldev Singh &

Kewal Krishan Singal

 

 

 

 

 

 

 

1481

QSAR analysis of analogs of bis[2-(acylamino)- phenyl] disulfides, 2-(acylamino)benzenethiols and S-[2-(acylamino) phenyl] alkanethioates as antihyperlipidemic agents

 

IPC: Int.Cl.7 C 07 C 321/28 // A 61 P 3/06

The study suggested that the cholesteryl ester transfer protein inhibitors as determined in the human are having significant correlation with steric (Principle moment of inertia of X-component) and thermodynamic (logP and bend energy) properties of the molecule.

 

 

 

 

P Hanumantharao, S V Sambasivarao,

L K Soni, A K Gupta & S G Kaskhedikar*

 

 

 

 

 

 

 

1487

Phenylalanine and isoleucine containing protein-based polymers as new biomaterials: Synthesis and solid state properties

 

IPC: Int.Cl.7 C 08 L

 

Plastic protein-based polymers are designed and synthesized to verify their thermal stability.

 

Poly(FVGVP)

Poly(IVGVP)

 

 

A Ramesha Baba, D Channe Gowda* &

K Udaya Sankar

 

 

 

 

 

 

 

 

 

 

1494

1,8-Dihydroxyanthraquinone derivatives from rhizomes of Rheum emodi Wall.

 

IPC: Int.Cl.7 A 61 K 31/122

Two 1,8-dihydroxyanthraquinones isolated from rhizomes of Rheum emodi Wall. have been characterized as 6-methyl-rhein 1 and 6-methyl-aloe-emodin 2 by spectral data and chemical studies.

 

 

1        R = H, R1 = COOH

2        R = H, R1 = CH2OH

 

 

Sudhir S Singh*, Satish C Pandey,

Rajesh Singh & Santosh K Agarwal

 

 

 

 

Notes

 

 

 

1497

A novel synthesis of 1-(1-aza-2-arylvinyl)-2-[(1E)-2-arylvinyl]-4-(phenylmethylene)-2-imidazolin-5-ones

 

IPC: Int.Cl.7 C 07 D

A simple and novel procedure for the preparation of the title compounds is described. Treatment of azl­actone (4-benzylidene-2-methyloxazolin-5-one) with hydrazine hydrate gives, a-acetamido-cinnam­hydra­zide, which with aromatic aldehydes produces N-(1-aza-2-arylvinyl)-2-(acetylamino)-3-phenylprop-2-en­a­mides. These on treatment with Schiff bases in acetic acid yield the title compounds.

 

 

T V Maruthikumar & P Hanumantha Rao*

 

 

 

 

 

 

 

1500

A new and convenient synthesis of 15H-16,17-dihydrocyclopenta[a]phenanthrene derivatives

 

IPC: Int.Cl.7 C 07 J

A new and general synthesis of title compounds 6a-e starting with 4-methylphenylsulphonylation of 2-(3,4-dihydro-1-naphthalenyl)ethanols 1a-e is described.

 

 

 

 

J A Parihar, M M Jaiswar & M M V Ramana*

 

 

 

 

 

 

 

 

 

1505

A convenient synthesis of g-methyl a-(alkylidene)-g-butyrolactones

 

IPC: Int.Cl.7 C 07 D 307/32

 

 

 

 

 

 

 

Jyoti B Shet, Chandan P Amonkar,

Vishnu S Nadkarni & Santosh G Tilve*

 

 

 

 

 

 

 

1509

Microwave accelerated high speed solution synthesis of peptides employing HATU/HOAt

 

IPC: Int.Cl.7 C 07 K

Synthesis of several peptides employing HATU/HOAt as coupling agent under microwave irradiation has been described. The coupling is found to be complete in 30 - 45 sec.

 

 

 

 

 

 

 

Naremaddepalli S Sudarshan &

Vommina V Suresh Babu*

 

 

 

 

 

 

 

1512

Microwave assisted rapid synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione

 

IPC: Int.Cl.7 C 07 C 13/10

Synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione with various alcohols has been achieved under microwave irradiation conditions within 7 min.

 

 

 

 

 

 

R Murugan & B S R Reddy*

 

 

 

 

 

 

 

 

 

1515

Microwave-assisted aromatic nucleophilic substitution reaction of chloronitrobenzenes with amines in ionic liquids

 

IPC: Int.Cl.7 C 07 C 25/06

 

 

 

Chetna Angrish, Anil Kumar & S M S Chauhan*

 

 

 

 

 

 

 

1519

Ultrasonically accelerated Knoevenagel condensa­tion reaction at room temperature in distilled water

 

IPC: Int.Cl.7 C 07 D 311/00

The condensation reaction of 4-oxo-4H-1-benzo­pyran-3-carbaldehyde with 3-methyl-1-phenyl­pyra­zolin-5(4H)-one has been carried out under ultra­sonic irradiation at room temperature in distilled water as solvent.

 

 

S S Shindalkar, B R Madje & M S Shingare*

 

 

 

 

 

 

 

1522

Synthesis of 3-[2-(4-nitrophenyl)­vinyl]­chromon-4-one by ultrasonic irradiation

 

IPC: Int.Cl.7 C 07 D 311/00`

Various 3-[2-(4-nitrophenyl) vinyl] chromon-4-ones have been synthesized  by ultrasonic activation  from corresponding  3-formylchromones and  4-nitro­phenyl­acetic acid.

 

 

N R Dalvi, B K Karale & C H Gill*

 

 

 

 

 

 

 

1524

CrO/Al2O3: Rapid oxidation of alcohols to carbonyl compounds in a solvent- free system

 

IPC: Int.Cl.7 C 07 C 49/00

Primary and secondary alcohols are efficiently oxidized to the corresponding carbonyl compounds using CrO3 supported onto alumina under solvent- free conditions. Over-oxidation of aldehydes to carboxylic acids and cleavage of carbon–carbon double bond is not observed.

 

 

 

A R Kiasat*, F Kazemi* & K Nourbakhsh

 

 

 

 

 

 

 

 

 

 

1527

CeCl3/Sm induced reductive cleavage of the S-S bond in disulfide: A novel method for the synthesis of b-thioesters, thiolesters and alkyl­phenyl sulfides

 

IPC: Int.Cl.7 C 07

Disulfide has been reduced by cerium trichloride and samarium to produce samarium thiolates. The “living” species react smoothly with a,b-unsaturated esters (nitriles), acyl halides or anhydrides and alkyl or benzyl halides to afford b-thioesters(nitrile), thioesters or sulfides under mild and neutral conditions.

 

 

 

 

 

 

Xue Li, Songlin Zhang & Yongmin Zhang*

 

 

 

 

 

 

 

1530

Titanium superoxide catalyzed selective oxidation of phenols to p-quinones with aq. H2O2

 

IPC: Int.Cl.7 C 07 39/04, 46/00

 

 

 

 

 

 

 

Gajanan K Dewkar,Tanveer M Shaikh, S Pardhy, Swati S Kulkarni & Arumugam Sudalai*

 

 

 

 

 

 

 

1533

Pd-catalyzed oxidative kinetic resolution of 2-azido-1-arylethanols

 

IPC: Int.Cl.7 C 07 C 15/00, C 01 G 55/00

(-)-Sparteine/ Pd (II) complex in combination with oxygen as stoichiometric oxidant catalyzes the oxidative kinetic resolution of β-azido alcohols 1 to afford the corresponding chiral 2-azido-1-arylethanols 2.

 

 

 

 

 

 

Iliyas Ali Sayyed, N S C Ramesh Kumar &

A Sudalai*

 

 

 

 

 

 

 

 

 

1536

Polyaniline-octylbenzenesulfonic acid: Characte­ri­zation and synthesis in normal and reverse phase

 

IPC: Int.Cl.7 C 07 C 309/28

An attempt to synthesize a polyaniline (Emer) which combines the two properties in one polymer.  Polyaniline –octylbenzenesulfonic acid is thus synthesized in direct and reverse phases. Elemental analysis and TGA show it to be  Emer 2.5 .OBSA 5.0 .5.0 H2O. Its solubility is 80% in TMU and conductivity is ~7 × 10-5 ohm-1cm-1.  IR spectra show that  it is in a low oxidation state as compared to Emeraldine and hence its conductivity is low, which may also be due to larger inter- chain distance caused by the bulky OBSA.

 

Naseer Ahmad*, Shabnam Naseer &

Michael Norman

 

 

 

 

 

 

 

Announcements

1538

Second International Symposium On Green/ Sustainable Chemistry

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.: International Classification, 7th Edition, 1999