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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

3,372

 

VOLUME  44B

NUMBER 6

JUNE 2005

 

 

CONTENTS

 

Rapid Communications

1231

Polymorphic study of donepezil hydrobromide

 

IPC: Int.Cl.7 C 07 D

A systematic study to screen the existence of polymorphism in donepezil hydrobromide, affords six polymorphic forms. Preparation, characterization and stability of the same are reported.

 

 

Chandrashekar R Elati, Pravinchandra J Vankawala, Subrahmanyeswara Rao Chalamala, Naveenkumar Kolla, Srinivas Gangula, Himabindu Vurimidi, Venkataraman Sundaram & Vijayavitthal T Mathad*

 
Papers

 

1236

A novel and short convergent approach for N-aryl-5-aminomethyl-2-oxazolidinone derivatives Linezolid and DUP-721f

 

IPC: Int.Cl.7 C 07 D

 

A new convergent and short approach for oxazolidinone class of antibacterial agents, Linezolid and DUP-721, is achieved by condensing 3-chloro-2-[(phenoxycarbonyl) oxy]propyl azide with aryl amine followed by reductive acetylation. This one pot approach for N-aryl-5-azidomethyl-2-oxazolidinone could provide access for rapid preparation of various oxazolidinone analogues.

 

 

G Madhusudhan*, G Om Reddy, J Ramanatham & P K Dubey

 

1239

Synthesis of 1-(n-hexyl-5-one)-2-chlorobenzimida­zole

 

IPC: Int.Cl.7 C 07 D 233/54

o-Phenylenediamine on condensation with urea gives the known benzimidazolin-2-one 2, which on reaction with phosphoryl chloride in the presence of catalytic amount of phenol yields the already reported 2-chlorobenzimidazole 6. The latter on  alkylation with       6-chloro-2-hexanone in the presence of K2CO3 in DMF medium gives the title  compound 7.

 

 

 

 

 

P K Dubey*, A Naidu, V Anandam & G Hemasunder

 

1243

Synthesis of 3H, 9H, 10H, 10aH-10-aryl-2-aryliminothiazolidino[4,5-b][1,5]benzodiazepines and their alkoxyphthalimide derivatives

 

IPC: Int.Cl.7 C 07 D

Synthesis and characterization of 3H, 9H, 10H, 10aH-10-aryl-2-aryliminothiazolidino[4,5-b][1,5] benzo­ diaze­ pines and their alkoxyphthalimide derivatives are described. Cyclization of 5-arylidene-2-arylimino­thiazolidin-4-ones 1a-i with o-phenylene­diamine in xylene furnish the corresponding 1,5-benzodiazepines 2a-i. In another reaction route, 1a-i when condensed with w-bromoalkoxyphthalimides 3a-c give 3-alkoxy­phthalimido-5-arylidene-2-aryliminothiazo ­lidin-4-ones 4a-a' which on cyclization with o-phenylene­diamine produce 9H, 10H, 10aH-3-N-(n-alkoxyphthalimido)-10-aryl-2-aryliminothiazolidino[4,5-b][1,5]benzodiaze­pines 5a-a' in good yields.

 

 

 Text Box: (i)

 

Text Box: (ii)

 

Text Box: 2a-i

 

Text Box: 1a-i

 

 

Bhawani Singh, Lalit K Baregama, Maqbool Ahmed, Neha Dixit & G L Talesara*

 

 

 

1248

Syntheses and spectral characterization of 2-aryloxy-5,5¢-bis(bromomethyl)-1,3,2-dioxa­phos­ pho­rinane 2-oxides

 

IPC: Int.Cl.7 C 07 D

The title compounds 3a-h are synthesised by the reaction of 2,2-bis (bromomethyl)-1,3-propane diol 1 with various arylphosphorodichloridates 2 in the presence of triethylamine in dry tetrahydrofuran at room temperature.

 

 

 

 

M F Stephen Babu, U Anasuyamma, M Venugopal &

C Naga Raju & C Suresh Reddy*

1252

Synthesis and semiempirical calculations of isatylidine, thioisatylidine and acenaphthylidine derivatives of imidazolidine, thiazolidine, oxazo­lidine and pyrimidinetrione

 

IPC: Int.Cl.7 C 07 D

The Knovenaegel type condensation of benzo­[b]thiophene-2,3-dione (thioisatin), indole-2,3-dione and acenaphthylene-1,2-dione with imidazo­lidine, oxa­zolidine, pyrimidinetrione and thiazolidine deri­vatives has been described. The newly synthesized products have been characterized by spectral (IR, 1H NMR, 13C NMR and mass) data. Correlation of experimental results and exclusive formation of anti-monocondensation products has been ascertained on the basis of semiempirical calculations.

 

 

 

R T Pardasani*, P Pardasani, B Gupta, A V Londhe & S Kohli

 

  

1257

Polyheterocyclic systems: Synthesis and biological activity of novel heterocyclic annelated compounds from 2,3,4,5-tetrahydro-1-benzazepin-5-one

 

IPC: Int.Cl.7 C 07 D

2-Amino-6-(4-methylphenylsulphonyl)-5,6-dihydro-4H-benzo[b]thieno[3,2-d] azepin-1-yl cyanide 3 is subjected to variety of annelation reactions to give compounds 4-8. Compound 8 when subjected to nucleophilic displacement reactions with different amines affords 12-substituted derivatives 12-15.

 

 

 

                                                6                                 7                                              14                               11

 

 

Peesapati Venkateswarlu* & Suresh Babu Sunkaraneni

 

1262

Synthesis, antimicrobial and antiinflammatory activities of 4-oxothiazolidines and their 5-arylidenes

 

IPC: Int.Cl.7 C 07 D 277/62 // A 61 P 31/04, 31/10, 29/00

Several new 2-[(aryl)-3-(acetyl­amino)-1,3-thia­zo­li­din-4-ones]-2-mercaptobenzo­thia­zoleS 4 and 2-[5-arylidene-2-phenyl-3-(acetylamino)-1,3-thiazoli­dine- 4-ones]-2-mercaptobenzothiazoles 5 from 2-mercapto­benzothiazole have been synthesised and tested for their antimicrobial and antiinflammatory activities. Their structures have been determined by spectral and chemical methods.

 

 

 

 

R Yadav, S D Srivastava & S K Srivastava*

 

 

1267

Synthesis and antimicrobial activities of oxa­dia­zoles, phthalazines and indolinones

 

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

A series of oxadiazoles 5, phthalizines 6-8 and indolinones 9,10 have been synthesized from 2-[oxyacetyl hydrazine]ethyl benzenes 3. The compounds are characterized and screened for their antimicrobial activities.

 

 

N P Shetgiri* & B K Nayak

 

1273

Preparation, characterization and antimicrobial activity of fatty alkenoates

 

IPC: Int.Cl.7 C 07 C // A 61 P 31/04

The preparation of 3¢-(2¢¢-hydroxy-4¢¢-methoxy­phenyl)-1¢-phenylpropenyl undec-10-enoate 4 and 1-stearyl-2-undecenyl glycol 5 from DCC-mediated esterification of undec-10-enoic acid 1 is described. Compounds 4 and 5 and some other fatty alkenoates have been screened for their antimicrobial activity.

 

 

Abdul Rauf* & Humaira Parveen

 

 

1277

On the mechanism of the cooxidation of pentan-1-ol with oxalic acid by dichromates and halochromates of heterocyclic bases

 

IPC: Int.Cl.7 C 07 31/125

Chromium(VI) reagents exhibit identical kinetic  behaviour in the cooxidation of pentan-1-ol with oxalic acid.

 

 

 

C Karunakaran* & S Suresh

 

 

 

 

 

 

 

1283

Hydroxylic solvent effects on the reaction rates of diazodiphenylmethane with 2-substituted cyclo­hex-1-enylcarboxylic and 2-substituted benzoic acids: Part II

 

IPC: Int.Cl.7 C 07 C 63/00

The rate constants for the reaction of dia­zo­diphenylmethane with 2-substituted cyclohex-1-enylcarboxylic acids, determined in butan-1-ol, 2-methylpropan-1-ol and ethylene glycol, together with the rate constants determined previously in methanol, ethanol, propan-1-ol and propan-2-ol, are correlated using the total solvatochromic equation, of the form log k = A o + sp* + aa  + bb,  the two parameter model  log k = Ao + sp*+ aa and the single parameter model log k = Ao  + bb, where p*, b and a  represent the solvent dipolarity/polarizability, solvent hydrogen bond acceptor basicity and   hydrogen bond donor acidity, respectively. The results obtained for 2-substituted cyclohex-1-enylcarboxylic acids are compared to the results for 2-subsituted benzoic acids under the same experimental conditions.

 

 

Ph2CN2 + RCOOH ® Ph2CHN2+ - O2CR

 

Gordana S Ušćumlić*, Jasmina B Nikolić & Vera V Krstić

 

 

 

 

 

 

 

1288

Immunostimulatory compounds from Vitex negundo

 

IPC: Int.Cl.7 A 61 K 31/56 // A 61 P 37/04

Two compounds, a lignan 1 and a steroidal glycoside 2 exhibiting immunostimulatory activity in oxyburst phagocytic assay using human polymorphonuclear cells have been isolated from the extract of Vitex negundo.

 

 

D D Singh, G Chitra, I P Singh & K K Bhutani*

 

 

 

1291

Sterols and flavonol glycosides from Melothria purpusila

 

IPC: Int.Cl.7 C 07 A 61 K 35/00

Two sterols ergosta-7.22-dien-3b,5a,6b-triol 1, 3-O-b-d-glucopyranosyl-ergosta-7,22-dien-5a,6b-diol 2 and three flavonol glycosides, quercetin 4¢-O-β-d-galactoside 3, kaempferol 3-O-b-d-glucosyl (1®2)-b-d-glucoside 4, and quercetin 3-O-b-d-glucosyl-(1®2)-b-d-galactoside-7-O-b-d-glucoside 5 have been isolated from Melothria purpusila.

 

 

         

1: R = H; 2: R = glc                       3: R1 = R2 = H, R3 = gal, R4 = OH;

                                                                                              4: R1 = R3 = R4 = H, R2 = glc(1-2)gal;

                                                                                                   5: R1 = glc, R2 = glc(1-2)gal, R3 = H, R4 = OH

 

Reena D Langoljam, Brajeshwari D, Kongbrailatpam & Warjeet S Laitonjam*

 

 

Notes

1295

A rapid and facile synthesis of isoxazolyl and pyrazolyl phenols from enaminoketones using montmorillonite under heterogeneous catalytic conditions

 

IPC: Int.Cl.7 C 07 D 261/00, C 07 D 231/00

A number of isoxazolyl and pyrazolyl phenols (4a-f and 5a-d) have been synthesized from 1-(2-hydroxyaryl)-3-dimethylamino-2-propen-1-ones 3a-f using montmorillonite as solid acid support.

 

 

 

 

 

G Jagath Reddy* & K Srinivasa Rao, Md Khalilullah & D Latha

 

 

 

 

1298

Synthesis and reactions of 4-(aminoaryl)- methylene-2-aryl-2-imidazolin-5-ones

 

IPC: Int.Cl.7 C 07 D 233/54

Benzimidic acid methyl esters on heating with glycine ester in toluene in presence of sodium acetate yield 4-(aminoaryl)­methylene-2-aryl-2-imidazolin-5-ones 2.

 

 

P M Shafi*, T D Sobha & P A M Basheer &

R Waibel

 

1301

ZrOCl2.8H2O as a new solid phase and recyclable catalyst for an efficient Knoevenagel condensation under solvent-free microwave irradiation conditions

 

IPC: Int.Cl.7 C 01 G 25/04

A new solid phase and recyclable catalyst for an efficient Knoevenagel condensation under solvent - free microwave irradiation conditions has been developed for universal applications in C-C bond formation.

 

 

 

 

T Yakaiah, G Venkat Reddy, B P V Lingaiah, P Shanthan Rao & B Narsaiah*

 

1304

Bismuth oxide perchlorate catalysed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones: An improved high yielding protocol for the Biginelli reaction

 

IPC: Int.Cl.7 C 07 D 239/00

Dihydropyrimidines are prepared by a one-pot cyclo­condensation of aldehydes, β-ketoesters and urea in acetonitrile by using bismuth oxide perchlorate as the catalyst for the first time.

 

 

Y Thirupathi Reddy, P Narsimha Reddy,
 B Sunil Kumar, G V P Rao & B Rajitha*

 

 

 

1307

Synthesis of 3-cyano and 3-cyano-4-methylcou­marins using phase transfer catalysis

 

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

Synthesis of 3-cyano and 3-cyano-4-methylcoumarins have been achieved by the reaction of 2-hydroxy­benzaldehydes/2-hydroxyacetophenones with mala­no­nitrile in biphase medium using phase transfer catalysis.

 

 

 

 

 

Seema, Surender Kumar & J K Makrandi*

 

1309

Dielectric activation of MnO2: Part 1 ¾ Oxidation of conjugated unsaturated alcohols

 

IPC: Int.Cl.7 C 07 C 9/00

A simplified methodology for the microwave induced activation of ‘wet’ manganese dioxide used in the oxidation of conjugated unsaturated alcohol is demonstrated. The method, apart from being rapid, offers the extra advantage of compatibility in a host of common organic solvents.

 

 

 

 

Tapan K Lai, Julie Banerji*, Asima Chatterjee & Bidyut Basak

 

1312

Amidation of amines with esters catalyzed by Candida antarctica lipase (CAL)

 

IPC: Int.Cl.7 C 07 C 211/01

Lipase catalyzed synthesis of amides from chiral esters with amines under mild condition.

 

 

 

 

Bo Yang, Yanjun Zhang, Shusheng Zhang*, Izumi T

 

 

 

1317

Acetonitrile: A convenient reagent for the one-pot preparation of perfumery nitriles from aldehydes

 

IPC: Int.Cl.7 C 07 C 47/00

Various aryl and alkyl nitriles have been prepared in high yields in one-pot process by refluxing various aldehydes and hydroxylamine hydrochloride in acetonitrile.

 

R=Anisyl-,. Cinnamyl-, Geranyl-, 4-OH-3MeOC6H4-,

                                                                                                        Decyl-, Dodecyl-, Citronellyl-

 

Vinod R Kanetkar*, Dhananjay D Zope & Y V V Subrahmanyam

 

1319

Theoretical study on the mechanism of alkylation at N-7 of guanine by few nitrogen mustards

 

IPC: Int.Cl.7 C 07 D 473/18

An idealized model of intermediate involved in alkylation reaction by nitrogen mustard is reported. The chances of forming carbonium ion intermediate in the alkylation of some drugs have been analysed.

 

 

P K Bhattacharyya & C Medhi*

 

1324

Chemical investigation of the seed oil of Strychnos potatorum and spectroscopic estimation of  linoleic and linolenic acids

 

IPC: Int.Cl.7 A 61 K

Analysis of seed oil is reported. The unsaponifiable matter contains steroids, sterols etc. (20.8%). The analysis of total fatty acids (60.4%) gives saturated fatty acids (49.1%) and unsaturated acids (50.9%) containing linoleic acid (8.18%) and linolenic acid (31.94%).

 

 

A K Indrayan*, Neeraj Kumar, P K Tyagi & Vishal Sharma

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

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