Indian Journal of Chemistry

 

Sect. B: Organic Chemistry including Medicinal Chemistry

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VOL. 51B

NUMBER 12

December 2012

 

CONTENTS

 

Papers

 

 

 

 

1731

A mild and efficient synthesis of bis(indolyl)methane derivatives catalyzed by monoammonium salt of 12-tungstophosphoric acid

 

A simple, highly rapid and efficient electophilic substitution reaction of indole with various aromatic aldehydes has been carried out using 5 wt% of monoammonium salt of 12-tungstophosphoric acid [(NH4)H2PW12O40] as a solid acid catalyst in acetonitrile to afford the corresponding bis(indolyl)methanes in excellent yields (84-95%) at room temperature. The heteropolyacid-based catalyst has the advantages of simple workup procedure, water insolubility with good activity and high yielding reaction for the synthesis of bis(indolyl)methane derivatives.

 

 

 

 

B Y Giri, B L A Prabhavathi Devi*, K Vijayalakshmi, R B N Prasad, N Lingaiah & P S Sai Prasad

 

Centre for Lipid Research, Indian Institute of Chemical Technology, Hyderabad 500 007, India

 

 

 

 

 

 

 

1738

Investigation of the structure-nonlinearity relation­ship of zederone from the rhizomes of Curcuma caesia Roxb.

Sesquiterpenoids 1, 2, 3, have been isolated from the dried rhizomes of Curcuma caesia Roxb. The purity of the compound 1 is rated 99.12-99.54% by RP-HPLC method. The structure of zederone, 1 has been elucidated by spectroscopy IR, 1H NMR, 13C NMR, DEPT, mass spectrometry and X-ray analysis. Second harmonic generation (SHG) efficiency of the compound 1 is found to be higher than that of KDP.

 

 

 

 

Satyavama D Asem & Warjeet S Laitonjam*

 

Department of Chemistry, Manipur University, Canchipur, Imphal 795 003, India

 

 

 

 

 

 

 

 

 

 

 

 

 

1743

Uncatalysed Knoevenagel condensation of 3-formyl­chromones in green media: Polyethylene glycol - 400 (PEG-400)

 

An efficient, rapid and environmentally benign method for the Knoevenagel condensation of 3-formylchromones with a variety of active methylene compounds in polyethylene glycol 400 (PEG-400) under microwave irradiation (MWI) has been developed. This protocol has been found to be applicable for condensation of pharmacologically active heterocyclics such as rhodanine, creatinine, pyrazol-5-one, barbituric acid, etc. with 3-formyl­chromones.

 

 

 

Suresh, Dhruva Kumar & Jagir S Sandhu*

 

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

 

 

 

 

 

 

1749

QSAR analysis on inhibitors of human dihydro­oro­tate dehydrogenase (hDHODH): The aryl carboxylic acid amide derivatives

QSAR analysis has been performed on a series of aryl carboxylic acid amide derivatives for the prediction of hDHODH inhibitory activity. Results of this study provide useful clues to design novel molecules as potent hDHODH inhibitors.

 

 

 

 

 

 

Vivek K Vyas* & Manjunath Ghate

 

Department of Pharmaceutical Chemistry, Institute of Pharmacy, Nirma University, Ahmedabad 382 481, India

 

 

 

 

 

 

 

 

 

 

 

 

Notes

 

 

 

 

 

 

1761

An efficient synthesis of lactarochromal from
6-amino-2,2-dimethylchroman-4-one

 

Lactarochromal, a metabolite of Lactarius deliciosus, has been synthesised employing formylation of preformed iodochromanone as the key step.

 

 

 

 

 

 

 

 

 

Vijayendra P Kamat*, Ratnakar N Asolkar & Janardan K Kirtany

 

Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India

 

 

 

 

 

 

 

1763

An improved and scalable process for the synthesis of a key intermediate for Etodolac, a non-steroidal anti-inflammatory drug

 

An improved and scalable method is developed for the synthesis of 7-ethyltryptophol, a key intermediate for Etodolac, a non-steroidal anti-inflammatory drug (NSAID) starting from commercially available 2-ethylphenyl hydrazine and dihydrofuran with H2SO4 as a catalyst in N,N-dimethylacetamide (DMAc)-H2O (1:1) as a solvent in 69% yield. The method is easy, inexpensive and reproducible and the process is clean, high yielding and operational­ly simple.

 

 

 

 

 

 

 

 

 

 

 

M Chandra Sekharayya, G Venkata Narayana,  Satish Nigam & G Madhusudhan*

 

Department of Research & Development

Inogent Laboratories Private Limited, A GVK BIO Company, 28A, IDA, Nacharam, Hyderabad 500 076, India

 

 

 

 

 

 

 

 

 

 

 

 

 

1767

Synthesis, characterisation and antimicrobial activity of 3-methyl-6-(aryl)-1-phenyl-1H-pyrazolo[3,4-b]py­ri­dine

 

A series of pyrazolopyridine has been synthesized starting from the corresponding 5-azido-3-methyl-1-phenylpyrazol-4-carboxaldehyde in one step. All the newly synthesized compounds have been screened for their antimicrobial activities.

 

 

 

 

 

 

 

Girisha K S, Balakrishna Kalluraya* & Vidyashree Jois H S

 

Department of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India

 

 

 

 

 

 

 

1771

A novel alkaloid, four alkaloid precursors and a coumarin from Feronia limonia

 

A new quinoline alkaloid has been isolated from the flowers of Feronia limonia along with four alkaloid precursors, one coumarin, a known steroid stigmasterol and p-coumaric acid. The structures of compounds have been elucidated on the basis of spectroscopic data and comparison with the literature.

 

 

 

 

 

 

 

P Pitchai, R Ulagi, P S Mohan * & R M Gengan

 

Department of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, India

 

 

 

 

 

 

 

 

 

 

 

 

 

1776

Conventional and microwave assisted synthesis of new benzotriazole derivatives and their antimicrobial potential

 

5-[2-(1,2,3-Benzotriazole)-1-yl-methyl]-2 [2′′-(substituted phenyl)-4′′-oxo-1′′,3′′-thiazolidine]-1,3,4-thiadiazoles, 1a-k has been further condensed with various aromatic aldehyde in presence of suitable base to yield 5-[2-(1,2,3-benzotriazole)-1-yl-methyl]-2-[5′′-(benzylidene)-2′′-substituted phenyl-4′′-oxo-1′′,3′′-thiazolidine]-1,3,4-thiadiazoles, 2a-k. All the above synthesized compounds have been screened for their antimicrobial activities.

 

 

 

 

 

 

D K Shukla*, J P Sen & A K Jain

 

Department of Chemistry, Govt. P. G. College, Gadarwara 487 551, India

 

 

 

 

1781

Acid catalyzed condensation of pyroglutamic acid with arylaldehydes: Synthesis of (3R, 7aS)-3-aryldihydropyrrolo[1, 2-c] oxazol-1, 5(3H, 6H) dione

 

A simple strategy has been described for the synthesis of (3R, 7aS)-3-aryldihydropyrrolo [1,2-c]oxazol-1,5 (3H,6H)-diones as bicyclic hemiaminals through acid  catalyzed condensation of pyroglutamic acid with arylaldehydes. This could be useful for the synthesis of complex natural products requiring α-substitution in proline or pyroglutamate skeleton.

 

 

 

 

 

Jagdish Prasad & Sharad Kumar Panday*

 

Department of Chemistry, Faculty of Engineering and Technology, M J P Rohilkhand University, Bareilly 243 006, India

 

 

 

 

 

 

 

1785

Annual Index

 

 

 

 

Authors for correspondence are indicated by (*)