Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

Website address: http://www.niscair.res.in; http://nopr.niscair.res.in

VOL. 49B

NUMBER 3

March 2010

CONTENTS

Papers

323

Synthesis of bis(arylamino)thiazoloylindoles as novel analogs of dendrodoine

T F Abbs Fen Reji*, S L Manju & K N Rajasekharan

Department of Chemistry, Nesamony Memorial Christian College, Marthandam 629 165, India

327

Lewis-acid mediated acetamidation of N-protected bromomethylindoles

A facile ZnBr₂-mediated acetamidation of various types of
N-protected 2/3-bromomethylindoles is reported. Upon interaction of bromomethylindoles with acetonitrile in the presence of anhydrous ZnBr₂ at reflux followed by aqueous work up led to the isolation of respective acetamidomethylindoles in good yields.

Vasudevan Dhayalan & Arasambattu K Mohanakrishnan*

Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India

335

Microwave-assisted synthesis of 1,2,4- triazolo[4,3-a] [1,8]naphthyridines using FeCl₃.6H₂O under solvent-free conditions

An efficient and convenient method for the synthesis of 9-aryl-6-(3-fluorophenyl)-1,2,4-triazolo[4,3-a][1,8]naphthyridines 8 from aryl aldehyde 3-(3-fluorophenyl)-1,8-naphthyridin-2-ylhydrazones 7 using FeCl₃.6H₂O under microwave irradiation is described.

K Mogilaiah*, R Shiva Prasad & J Kumara Swamy

Department of Chemistry, Kakatiya University, Warangal 506 009, India

Notes

340

The efficacy of unsupported and supported tungstophosphoric acid and its Fe - and Al - salts in the benzylation of arenes using benzyl alcohol and benzyl chloride

The efficacy of unsupported and supported tungstophosphoric acid and its Fe(III) and Al(III) salts for catalyzing the benzylation reaction using benzyl alcohol and benzyl chloride has been studied. The supports used are silica, zeolite H-ZSM-5 and an acidic clay montmorillonite K10. The significant observation of this investigation is the contrast in the activities of the unsupported and supported catalysts in the benzylation using benzyl chloride and benzyl alcohol, which may be a result of the ‘pseudo liquid phase’ behaviour of heteropoly compounds.

Amol S Tipnis, Deepak K Deodhar & Shriniwas D Samant*

Department of Chemistry, Institute of Chemical Technology, University of Mumbai, N M Parekh Marg, Matunga, Mumbai 400 019, India

346

Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4,5,6,7,8-hexahydroquinazolin-2(1H)-ones via three component cyclocondensation

3,4 Dihydropyrimidin-2(1H)-ones and 3,4,5,6,7,8-hexahydroquinazolin-2(1H)-ones have been synthesized from the condensation of ketones, aldehydes and urea/thiourea in presence of sodium tertiary butoxide by the solventless MWI process as well as the conventional process.

I T Phucho, A Nongpiur, R Nongrum & R L Nongkhlaw*

Department of Chemistry, North Eastern Hill University, Shillong, India

351

Improved synthesis of chalcones and pyrazolines under ultrasonic irradiation

An approach towards synthesis of various pyrazolines via green chemical routes is being reported.

Ragini Gupta*, Neetu Gupta & Anshu Jain

Department of Chemistry, Malaviya National Institute of Technology, Jaipur 302 017, India

356

Chemical constituents isolated from Andrographis paniculata

Phytochemical investigation of the aerial parts of Andrographis paniculata give diterpenic constituents andrographolide, 14-deoxy-11,12-didehydroandrographolide, 14-deoxyandrographolide, 3,14-dideoxyandrographolide, 14-deoxy-11-oxoandrographolide, 14-deoxy-12-hydroxyandrographolide, neoandrographolide, andrographiside and 14-deoxyandrographiside. The structures of these compounds have been established on the basis of spectral data analysis.

Poonam Kulyal*, U K Tiwari, A Shukla & A K Gaur

Department of Chemistry, A.N.D.N.N.M. College, C.S.J.M. University, Harsh Nagar, Kanpur 208 012 India

360

Microwave enhanced, solvent free green protocol for the production of 3,4-dihydropyrimidine-2-(1H)-ones using AlCl₃.6H₂O as a catalyst

3,4-Dihydropyrimidine-2-(1H)-ones are synthesized via a multicomponent reaction of aldehyde, urea or thiourea and 1,3-dicarbonyl compounds using microwave irradiation catalyzed by 10mol% AlCl₃.6H₂O under solvent free conditions. The catalyst being reported here is cheap, safe to handle and the whole procedure is eco-friendly.

Dhruva Kumar, Suresh & Jagir S Sandhu*

Department of Chemistry, Punjabi University, Patiala 147 002, India

364

Synthesis and anti-inflammatory activity of fluorinated propanedione derivatives

A new series of 1-(2`,4`-difluorophenyl)-3-(substituted phenyl)-1,3-propanediones have been synthesized. The synthesized compounds were subjected to anti-inflammatory activity testing with promising results

Arpita H More & C S Ramaa *

Department of Pharmaceutical Chemistry, Bharati Vidyapeeth’s College of Pharmacy, Sector 8,

C. B.D. Belapur, Navi Mumbai 400 614, India

368

Synthesis and antimicrobial evaluation of ethoxyphthalimide derivatized spiro [indole-3,5′-(1,3)thiazolo(4,5-c)isoxazol]-2(1H)-ones via ring closure metathesis

The synthesis of 3′-{(4-substituted phenyl-1-N-ethoxyphthalimido-6′-pyridin-2-yl}-3,3a′-dihydro-6′H-spiro[indole-3,5′-[1,3]thiazolo[4,5-c]isoxazol]-2(1H)-ones 6a-d has been achieved through a five step pathway Structural confirmation of the synthesized compounds has been accomplished by IR, ¹H NMR, and mass spectral data. Final compounds have been screened for their antimicrobial activity.

Bhawana Thadhaney, Devendra Sain, Gangotri Pemawat & G L Talesara*

Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, M. L. Sukhadia University,
Udaipur 313 001, India

374

Two new compounds from the stem of Nerium oleander

4-Oxooctyl-2-hydroxyundecanoate 1 is obtained as white powder from the stem of Nerium oleander. The structure is confirmed by spectral and analytical methods.

Pallavi Sharma, Yogesh K Gupta, M C Sharma & M P Dobhal*

Natural Products Laboratory, Department of Chemistry, University of Rajasthan, Jaipur 302 055, , India

379

An expeditious synthesis of syringaldehyde from para-cresol

Syringaldehyde has been prepared from p-cresol via a three step reaction sequence in overall yield of 59-67%. The synthesis involves solvent free bromination followed by high pressure and temperature methoxilation and catalytical oxidation. The use of cupric chloride as a catalyst in two key steps i.e. methoxilation in aromatic ring and oxidation of aromatic methyl to aldehyde is not only novel but also renders the process more viable.

A K Tripathi*, J K Sama & S C Taneja

Indian Institute of Integrative Medicines (CSIR), Canal Road, Jammu 180 001, India

382

Claisen-Schmidt condensation under solvent-free conditions

Claisen-Schmidt condensation of 2-(4-acetyl-phenylamino)-3-(4-chlorophenyl)-1,8-naphthyridine 3 with various aromatic aldehydes under solvent-free conditions to prepare α-β-unsaturated ketones 4 using solid NaOH as catalyst has been described.

K Mogilaiah*, T Kumara Swamy, A Vinay Chandra N Srivani & K Vidya

Department of Chemistry, Kakatiya University, Warangal 506 009, India

386

Polyphenols from the roots of Plumbago rosea

Phytochemical investigation of the roots of ethyl acetate extract of Plumbago rosea (Plumbaginaceae) on column chromatography yield flavonoids: myricetin-3,3′,5′,7-tetra methyl ether, ampelopsin-3′,4′,5′,7-tetra methyl ether; carboxylic acids: plumbagic acid and roseanoic acid.

1

2

3	4

S Ariyanathan *, Ariamuthu Saraswathy, G Victor Rajamanickam & Joseph D Connolly

Centre for Advanced Research in Indian System of Medicine (CARISM), SASTRA University, Thanjavur 613 402, India

390

Microwave-enhanced Knoevenagel condensation catalysed by NH₂SO₃NH₄

NH₂SO₃NH₄ catalyses the efficient Knoevenagel condensation of aromatic aldehydes 1 with active methylene compounds 2 in solvent-free conditions under microwave irradiation to give arylidene derivatives 3.

K Mogilaiah*, H Sharath Babu, K Vidya & K Shiva Kumar

Department of Chemistry, Kakatiya University, Warangal 506 009, India

394

Corrigendum

Authors for correspondence are indicated by (*)