Indian Journal of Chemistry

Sect. B : Organic Chemistry including Medicinal Chemistry

VOL. 42B

NUMBER 3

MARCH 2003

 

CONTENTS

 

 

Rapid Communication

 

 

593

Synthesis and cyclooxygenase (COX-1/ COX-2) inhibiting property of 3,4-diarylfuranones

Synthesis of a series diarylfuranones as potent COX inhibitors has been accomplished via aldol type condensation or oxidative cyclization of phenacyl ester. Detailed SAR within the series along with the anti-inflammatory activity has been investigated.

 

 

 

 

 

 

Manojit Pal, Venugopal Rao Veeramaneni, Srinivas Padakanti, Murali Nagabelli,

Akhila Vanguri, Premkumar Mamnoor,

Seshagiri Rao Casturi, Parimal Misra, Ramesh Mullangi & Koteswar Rao Yeleswarapu*

 

 

 

 

 

 

 

 

 

 

602

InCl3.3H2O: An efficient Lewis acid catalyst for stereoselective O-glycosidation reactions of per-O-acetylglycopyranosyl trichloroacetimidates

InCl3.3H2O catalyses O-glycosidation of per-O-acetylglycopyranosyl trichloroacetimidates with a variety of alcohols. The reaction proceeds with high yields and diastereoselectivity in favour of the 1,2-trans glycosides.

 

 

 

1,2-trans-glycoside
yields 73-91%
de 87-100%

 

 

 

Rina Ghosh, Avijit Chakraborty & Dilip Kumar Maiti

 

 

 

 

 

 

     

 

Papers

 

 

 

605

A facile synthesis of 4-oxo-1,2,3,4-tetra­hydro­pyrido[3¢,2¢:4,5]furo[3,2-d]pyridines: A new tri­cyclic heterocyclic ring system

The synthesis of 4-oxo-1,2,3,4-tetrahydropyrido-[3¢,2¢:4,5]furo[3,2-d]pyridines and furo[2,3-b] pyridines by a facile method is reported

 

 

 

 

K Srinivas, D Maitraie , P Shanthan Rao &
B Narsaiah*

 

 

 

 

 

 

 

611

Synthesis of 3-aryl and 3-aryl-3,4-dihydro­iso­cou­marins

A convenient route for the syntheses of 3,4-dihydroisocoumarins using literature procedures is reported.

 

 

 

 

 

Hafiz B Ahmad, Nasim H Rama*,

Mazhar Hussain, M T Hussain, M M Qasim, S Hameed, M A Malana & A Malik

 

 

 

 

 

 

 

 

 

616

Chemistry of benzocycloheptenones: Part I — Synthesis of 2,5-disubstituted-1,3,4-thia/oxa­dia­zoles as biologically active heterocycles

A series of new thia/oxadiazoles ring systems fused to benzocyclohepten-5-ones is reported.

 

Venkateswarlu Peesapati* &

Srikant Venkata Chitty

 

 

 

 

 

 

 

621

Synthesis of biologically active thiazolo-benzo­pyranyl–s-triazine derivatives

Synthetic utility of 1 to synthesize various biologically active heterocycles like 2-5 is reported

 

V V Mulwad* & Jyoti M Shirodkar

 

 

 

 

 

 

 

627

Synthesis and antimicrobial activity of 3-methoxy-
4-[4-chloro phenyl thioethoxy]-5-cyano­phenyl benzaldehyde and its interme­diates

Synthesis of 3-methoxy-4-[4-chlorophenyl thioethoxy]-5-cyanophenyl benzaldehyde, an important intermediate in the synthesis of 2,5- trans-diaryl tetrahydrofuran is reported.

 

B Balram, B Ram, D Subhadra & V Anand*

 

 

 

 

 

 

 

 

631

Synthesis and antimicrobial profile of 5-imidazolinones, sulphonamides, azomethines, 2-azetidinones and formazans derived from 2-amino-3-cyano-5-(5¢-chloro-3¢-methyl-1¢-phenyl pyra­zol-4¢-yl vinyl)-7,7-dimethyl-6,7-dihydro ben­­­zo (b) thiophenes

Several new substituted benzo(b)thiophenes 2,
5-imidazolinones 3a-j, sulphonamides 4a-j, azomethines 5a-j, 2-azetidinones 6a-j and formazans 7a-j have been reported.

 

 

 

 

J M Desai & V H Shah*

 

 

 

 

 

 

 

636

Synthesis of pyrazoline, pyrimidine and 1,5-benzodiazepine derivatives of 1,8-naphthyri­dine and evaluation of antibacterial activity

A series of new bis-1,8-naphthyridines 4, 1,8-naphthyridinyl 2-pyrazolines 5, 2-thioxopyrimidines 6 and 1,5-benzodiazepines 7 have been synthesized from 2-aminonicotinaldehyde 1.

 

 

 

K Mogilaiah* & G Rama Sudhakar

 

 

 

 

 

 

 

641

Variations in the essential oil composition of Persea bombycina (King ex Hook. f.) Kost and its effect on muga silkworm (Antheraea assama Ww)— A new report

Dodecanal, decanal, 11-dodecenal, undecanal, (E)-nerolidol, decanoic and dodecanoic acids are identified as a major essential oil compositions of Persea bombycina, a primary food plant of the muga silkworm. High aldehyde and low acid content in oil show positive effect on the growth of silkworm (Antheraea assama) and cocoon quality.

 

S N Choudhury* & Ingrid Vajczikova

 

 

 

 

 

 

 

 

 

Notes

 

 

 

648

Novel synthesis of 4',5,7-trihydroxy-3'-metho­xy­­flavanone (homoeriodictyol)

Synthesis of 4',5,7-trihydroxy-3'-methoxyflavanone from alkaline condensation of phloroacetophenone and vanilline is reported.

 

N P Shetgiri* & L N Rege

 

 

 

 

 

 

 

651

A novel approach to the synthesis of the purine anti-viral agent gancyclovir

Gancyclovir 8 has been synthesized from compound 1 in several steps.

 

Reyhaneh Sariri* & Gholamhosein Khalili

 

 

 

 

 

 

 

655

A novel one-pot synthesis of 2-arylquinolines through cascade reactions mediated by samarium reagents

A novel one-pot synthesis of 2-arylquinolines 4 from o-nitrobenzaldehydes and a-haloketones through SmI3 and Sm(II) mediated cascade reactions has been reported.

 

Xuesen Fan & Yongmin Zhang*

 

 

 

 

 

 

 

658

Synthesis of 6-aryl-2-(2-phenyl-1,8-naphthyri­dine-3-carbonyl)-4,5-dihydropyridazin-3(2H)-ones

Synthesis of 1,8-naphthyridine-3-carbonyl-3(2H)-pyridazinones 4 starting from a useful synthon 2-phenyl-1,8-naphthyridine-3-carboxylic acid hydrazide 1 has been reported.

 

K Mogilaiah & G Kankaiah

 

 

 

 

 

 

 

 

661

Synthesis and crystallographic characterization of some derivatives of benzimidazole

 

 

T Mohan Das, Chebrolu P Rao*, Nattinen Kalle & Kari Rissanen

 

 

 

 

 

 

 

666

Synthesis of w-unsaturated O-protected glucosides as precursors for unsaturated neutral bolaforms

The Lewis acid catalyzed glycosylation reaction of b-peracetylated sugar derivative (glucose) with terminally unsaturated C3-C11-alkenols is used in the synthesis of some C3-C11-alkenyl glucopyranosides as precursors for unsaturated neutral bolaforms.

i. Ac2O, NaOAc  (ii) ROH (3), SnCl4

iii MeOH; Et3N:H2O

 

S Konstantinović*, J Predojević, S Gojković & V Pavlović

 

 

 

 

 

 

 

670

Alkali cleavage of a,a-disubstituted b-keto­esters, nitriles and b-diketones

 

 

T H Bennur & N N Joshi*

 

 

 

 

 

 

 

672

Selective reduction of aromatic nitro compounds to azoxy compounds with zinc/aluminum chloride reagent

Aromatic azoxy compounds have been prepared in good yields by the selective reduction of aromatic nitro compounds with Zn/AlCl3 reagent.

 

Dilip Kumar Dutta

 

 

 

 

 

 

 

 

 

 

674

Solid state reactions of some isoxazole derivatives

The reaction of 4-benzalamino-3-methyl-5-styryl isoxazole with m-CPBA in solid state leads to secondary amides rather than expected oxaziridines.  Interaction of 4-amino-3-methyl-5-styrylisoxazole with phthalic, maleic and succinic anhydrides in solid state gives the products with an opening of anhydride ring which are then cyclized with acetic anhydride to give diimides.

 

 

 

E Rajanarendar* & Md Afzal

 

 

 

 

 

 

 

 

 

 

 

678

Chloro- or bromo-trimethylsilane induced rapid and quantitative acid-ester conversion for steroid based alcohols with various carboxylic acids under solvent free conditions

Steroid based higher alcohols are rapidly esterified in quantitative yield with a  number of carboxylic acids in the presence of TMSCl or TMSBr generally  under solvent free conditions

 

 

 

Papori Goswami, Saroj Hazarika,

Parinita Borah & Pritish Chowdhury*

 

 

 

 

 

 

 

 

 

 

683

Synthesis of some benzothiazepins and their antimicrobial activities

A series of 2-[(substitutedphenyl)-4-(substituted phe­nyl)]-3, 3-dihydrosubstituted-1, 5-benzothiazepin 3aa-3gd has been synthesized, characterized and screened for their antimicrobial activity.

 

 

 

N P Shetgiri* & B K Nayak

 

     

 

 

 

 

 

 

 

 

 

688

Synthesis and antibacterial activity of pyrimido[4,5-b]quinolines

A concise one-pot synthesis of pyrimido[4,5-b]                 quinolines has been achieved from the potential substrates 2-chloro-3-formylquinolines and guanidine nitrate. All the synthesized compounds have been biologically screened for their antibacterial activity.

 

 

 

R Nandha Kumar, T Suresh & P S Mohan*

 

 

 

 

 

 

 

 

 

 

690

Synthesis of new 4-aryl/alkyl-1-(5¢,5¢-diphenyl-4¢-oxo-1¢H-4¢,5¢-dihydro-imidazolidin-2¢-yl)-3-hy­dro­xy-1,2,4-triazolidine-5-thiones as potential anti-cancer agents

Thermal cyclization of 2-carbethoxy-(5¢,5¢-diphenyl-4¢-oxo-1¢H-4¢,5¢-dihydroimidazolidin-2¢-yl)hydrazine with aryl/alkylisothiocyanates afford the title compounds 3. Their anti-bacterial, anti-fungal, anthelmintic and anti-cancer activities are reported.

 

3

 

 

Prasanna A Datar, P Y Shirodkar* &

K R Panikkar

 

 

 

 

 

 

 

 

 

 

695

Synthesis of biologically important new 1, 4-benzothiazines bearing thiazole substituted aroyl moiety

2-[2'-Hydroxy-5'-(2''-substitutedthiazol-4''-yl)benzoyl]-3-(4'-substitutedphenyl)-1, 4-benzothiazines 4 have been synthesized from 2-acyl-4-(2'-substitutedthiazol-4'-yl)phenols 1 and their antimicrobial activities are evaluated.

 

4                             

 

 

R D Ingle, V E Bhingolikar, S P Bondge &

R A Mane*

 

 

 

 

 

 

 

Authors for correspondence are indicated by (*)