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Indian Journal of Chemistry

Sect. B : Organic Chemistry including Medicinal Chemistry

 

 

VOLUME 42B

NUMBER 10

OCTOBER 2003

 

CONTENTS

Rapid Communications

 

 

 

2556

Environmentally benign reaction: Synthesis of sydnone chalcones under solvent-free conditions

An easy, simple and eco-friendly synthesis of 4-(1-oxo-3-aryl-2-propenyl)-3-arylsydnones is reported by grinding 4-acetyl-3-arylsydnones with various aryl aldehydes under solvent free conditions.

 

 

 

Balakrishna Kalluraya* & Ganesha Rai

 

 

 

 

Papers

 

 

 

2558

Synthesis of new heterocycles containing pyrazole

New heterocyclic systems derived from pyrazole associating different nuclei such as pyrimidobenzimidazole, pyrimidopyrimidine, thiazolopyrimidine and pyrazolylpyridone have been synthesized by the treatment of some bisnucleophiles with acetoacetylpyrazole resulting from dehydroacetic acid.

 

 

 

 

B Djerrari, J Fifani, N H Ahabchane, E M Essassi*, B Garrigues & M Pierrot

 

 

 

 

 

 

 

2563

A convenient short synthesis of poly­substituted 3,4-dihydropyridine-2(1H)-thiones

4-Substituted- 3,4-dihydro-5-cyano-6-methyl-2(1H)- pyri­d­ones  obtained by reacting a,b-unsaturated acid chlo­rides with  3-aminocrotononitrile are converted quanti­ta­tively to the  corresponding novel hydrogenated pyridine­thiones 3 by  Lawesson’s reagent 2a.

 

 

S K Dutta Chowdhury, Mili Sarkar , A Chatterjee & Kumar K Mahalanabis*

 

 

 

 

 

 

 

2567

 

Synthesis of novel heterocyclic compounds from 6H-[2]-benzopyrano[4,3-c]quinolin-6-one and 2,3-diphenylfuro[3,2-c]quinolin-4-(5H)-one

11- Chloro-6H-[2] - benzopyrano[4, 3 - c]quinolin-6-ones
1a-g/4-chloro-2,3-diphenylfuro[3,2-c]quinoline 6a-g on tre­­at­­ment with sodium azide, o-phenylenediamine, anthra­nilic acid and benzoic acidhydrazide separately afford novel hetrocyclic compounds 2a-g/7a-g, 3a-g/8a-g, 4a-g/9a-g and 5a-g/10a-g respectively.

 

 

V V Mulwad* & Manojkumar V Lohar

 

 

 

 

 

 

 

2573

Electrophilic substitution of indoles: Part XXI – Further investigation on the formation of the benzazepinone skeleton

An interesting observation has been made during the electrophilic substitution of indole with 5,5-dimethylcyclohexane-1,3-dione resulting in the synthesis of 2,3,4,5,10,11-hexahydro-3,3-dimethyl-11-(indol-3-yl)-dibenz[b.f]azepin-1- one system. The reactions with 2-methyl- and 3-methylindoles result in the formation of only 1:1 product. The structures of the products have been settled on the basis of their UV, IR, 1H and 13C NMR spectral studies and MS analysis.

 

 

J Banerji*, A Chatterjee*, M Saha,
P Mukherjee & S Kanrar

 

 

 

 

 

 

 

 

2577

Enzymatic synthesis of butyl acetate using Rhizomucor miehei lipase: Parametric study

Immobilized lipase from Rhizomucor miehei (Lipozyme IM-20) is used to catalyze the esterification reaction between acetic acid and butanol to synthesize butyl acetate in n-hexane. Effect of various reaction parameters such as substrate concentration, enzyme concentration, reaction temperature and molar ratio have been investigated for maximization of yields.

 

 

 

 

G Vijay Kumar & M Narasimha Rao*

 

 

 

 

 

 

 

2583

Synthesis of thiadiazolo-s-triazines for their antiviral activity based on QSAR studies

 

 

 

V K Pandey*, Z Tusi , M Tandon, M N Joshi & S K Bajpai

 

 

 

 

 

 

 

2589

Synthesis, spectral and antimicrobial evaluation of some new 8-membered phosphorus heterocyclic compounds

The title compounds 4a-i are synthesized by reacting 2,2-bis (2-hydroxy-5-chlorophenyl)-1,1,1-trichloroethane 1 with thiophosphoryl chloride 2 in the presence of triethylamine in dry toluene to form the intermediate 3, which on subsequent reaction in situ with different phenols/thiophenols under the same conditions afford the compounds 4a-i.

 

 

K Ananda Kumar, C Suresh Reddy* &
C Devendranath Reddy

 

 

 

 

2595

Synthesis, spectral studies and biological profile of pyrazolines, isoxazoles, cyano­pyridines having phenothiazine moiety

Several new 3,7-bis[substituted benzalacetoacetamido]-phenothiazines 2a-j, 3,7-bis[1˘-N-H-/ acetyl-5˘ –aryl-2˘-pyrazolin-3˘-yl-acetamido]phenothiazines 3a-j, 4a-j, 3,7-bis[5˘-arylisoxazol-3˘-yl-acetamido]pheno­thia­zines 5a-j and 3,7-bis-[2˘-amino-3˘-cyano-4˘-aryl-pyridin-5˘-yl-acet­a­mi­do]phenothiazines 6a-j have been synthe­sised and screened for antimicrobial activity. The products display moderate to good or comparable activity with known standard drugs.

 

 

J M Desai & V H Shah*

 

 

 

 

 

Notes

 

 

 

2601

N, N˘-Carbonyldisaccharin: A new­ condens­ing agent for the synthesis of amides, esters and peptides

 

 

 

L D S Yadav*, Suman Dubey & Amrish Singh

 

 

2604

Zn(OTf)2-catalyzed three-component, one-pot, condensation reaction: An efficient synthesis of 4-aryl-5-substituted-6-methyl-3,4-dihydropyrimidin-2(1H)-ones

 

 

 

Hui Xu & Yan-Guang Wang*

 

 

 

 

 

 

 

2608

Synthesis of N-tert-butyl- N ˘(N)- (1-aryl-1,4-dihydro-6-methylpyridazine-4-oxo-3-carbo­nyl)-N (N˘ )-(substituted) benzoylhydrazine

Two series of N-tert-butyl- N˘(N)- (1-aryl-1,4 -dihydro-6-methylpyridazine-4-oxo-3-carbonyl)- N(N˘)-(substi­tu­ted)­ benzoyl­hydrazines have been synthesized. The preliminary bioassays indicate that some compounds show fungicidal activity.

 

 

Xia-Juan Zou & Gui-Yu Jin*

 

 

 

 

 

 

 

2612

Solid superacid catalyzed one step synthesis of coumarins

Coumarins are successfully synthesized by the reaction of phenols with ethyl acetoacetate or methyl acetoacetate in the presence of ZrO2/SO42- or TiO2/SO42- solid superacid.

 

 

Tongshou Jin*, Junjie Guo, Yahui Yin, Huimin liu & Tongshuang Li

 

 

 

 

 

 

 

2615

Microwave thermolysis: Part III—A rapid and convenient coupling of 2-naphthols in solvent-free condition

 

 

 

H M Meshram*,G Sudershan Reddy,
M Muralidhar Reddy,B Eeshwaraiah  &
J S Yadav

 

 

 

 

 

 

 

 

2618

Mild and efficient oxidation of pyrazolinyl-1,8-naphthyridines to pyrazolyl-1,8-naphthy­ri­dines mediated by cerium (IV) ammonium nitrate under microwave irradiation

An efficient and convenient method for the oxidation of pyrazolines 3 to pyrazoles 4 using CAN under microwave irradiation is reported.

 

 

K Mogilaiah*, N Vasudeva Reddy & R Babu Rao

 

 

 

 

 

 

 

2622

An unusual outcome in the Wittig olifination of artemisinin and its derivatives under micro­wave irradiation

Artemisinin type 1,2,4-trioxanes give ring contracted derivatives on treatment with triphenylcarbethoxy­methylphosphonium chloride and Amberlyst-A21 in THF under microwave irradiation.

 

 

Biswajit Kalita, Nabin C Barua* & Ghanashyam Bez

 

 

 

 

 

 

 

2625

New synthetic methods : Part I—Regio­selective 1,2-transposition of carbonyl group in carbocyclic and heterocyclic ketones

Novel 1,2-carbonyl transposition reaction has been successfully applied to heterocyclic and carbocyclic systems.

 

 

Madhukar S Chande* & Anand P Amle

 

 

 

 

 

 

 

2628

Use of S-proline as chiral  auxiliary in a-alkylations of carboxylic acids

Use of S-proline as auxiliary in a-alkylations of carboxylic acids results in Se-face approach of the electrophile.

 

 

Stuti Srivastava, Lalit N Goswami &
Dinesh K Dikshit*

 

 

 

 

 

 

 

 

2632

Samarium triiodide catalyzed deprotection of 1,1- diacetates

Catalyzed by samarium triiodide, cleavage of the 1,1- diacetates proceeds efficiently and selectively to give the corresponding aldehydes under neutral conditions.

 

 

Xiaoxia Wang & Yangmin Zhang*

 

 

 

 

 

 

 

2635

Deprotection of 1,3-oxathiolanes to carbonyl compounds with montmorillonite K10

A facile and clean method for the deprotection of different aliphatic and aromatic 1,3-oxathiolanes 1 to the corresponding carbonyl compounds 2 using montmorilonite K10 in good yields under mild and environmentally compatible conditions has been reported.

 

 

 

S M S Chauhan*, Anil Kumar & B B Sahoo

 

 

 

 

 

 

 

2638

Selective conversion of thioamides and thioureas to their oxygen analogues using quinolinium fluorochromate

A convenient and selective method for the conversion of thioamides and thioureas to their corresponding carbonyl compounds using quinolinium fluorochromate (QFC) is reported.

 

 

M Tajbakhsh*, I Mohammadpoor-Baltork*  & S K Alimohammadi

 

 

 

 

 

 

 

2641

A facile conversion of aromatic esters to amides by using lithium amide under mild reaction condition

One pot conversion of aromatic esters to amides by using lithium amides derived in situ by reacting n-butyl lithium with a primary or secondary amine at 0°C in diethyl ether as the solvent, has been reported.

 

 

 

Dibakar C Deka*, Biswajit Purkayastha & Maumita Paul

 

 

 

 

 

 

 

 

2643

Preparation, spectroscopy and electro­chemis­try of some ferrocenyl Schiff base derivatives with NLO responses

Eleven new ferrocenyl Schiff bases have been synthesized. These compounds have been studied by electronic absorption spectrum, cyclic voltammetry and Kurtz powder SHG measurements. The compounds show electron transfer abilities and NLO responses. The largest SH value is as large as 190 times that of urea reference.

 

 

Bangjing Li,* Guosheng Huang, Ling Shi, Wanyi Liu, Baohua Chen, Xiaoli Wu

 

 

 

 

 

 

 

2649

Synthesis of new biologically active aryl­furanylmethyltriazinones and their anti­bacterial activity studies

The synthesis and antibacterial screening of some triazinones carrying arylfuranyl moieties have been carried out.

 

 

B Shivarama Holla*, M K Shivananda,  B Veerendra & K Subrahmanya Bhat

 

 

 

 

 

 

 

2652

Synthesis and anitmicrobial activity of 5-[(4-aroyl)aryloxymethyl]-2-(4-methylphenyl)­ami­­no-1,3,4-thiadiazoles and 5-[(4-aroyl)­aryl­oxy­methyl]-4-(4-methylphenyl)-3-mercapto-4H-1,2,4-triazoles

1,3,4-Thiadiazoles 5a-d and 3-mercapto-1,2,4-triazoles 6a-d have been obtained by intramolecular cyclization of aroyl aryloxyacetic thiosemicarbazides using conc.H2SOand 2N NaOH.

 

 

B S Sudha, S Shashikanth* & Shaukath Ara Khanum

 

 

 

 

 

 

 

2657

Anticonvulsant activity of semicarbazone derivatives of Mannich bases

A series of semicarbazones of semicarbazide/p-chlorophenyl semicarbazide and Mannich bases of acetophenone/p-chloro­acetophenone has been synthesized and their anticonvulsant activity screened against MES and scPTZ test. p-Chlorophenyl semicarbazone of N,N-dimethylaminopropiophenone has been found to be the most active in all these tests.

 

 

S N Pandeya*, V Sowmyalakshmi, S S Panda, A Pandeya & J P Stables

 

 

 

 

 

2662

Synthesis of olivacene, a constituent of Archilejeunea olivacea

Synthesis of olivacene from b-cyclocitral is reported.

 

b-cyclocitral                            olivacene

 

Shrivallabh P Kamat*, Asha M D’Souza & Shashikumar K Paknikar

 

 

 

 

 

 

 

2665

A new triterpene from Adiantum lunulatum Burm.

Isolation and characterization of a new hopane tpye triterpene, 3b-acetoxy-6a-hydroxy-hop-15,17(21)-diene 1, from the petrol extract of Adiantum lunulatum has been reported.

 

 

K S Mukherjee, S Mondal, S M A Sohel,

P Mukherjee, D Chatterjee &

G Brahmachari*

 

 

 

 

Book Review

 

 

 

2668

Trends in Carbohydrate Chemistry, edited by P L Soni

 

Reviewer: Prof. Nirmolendu Roy

 

 Authors for correspondence are indicated by (*)