Indian Journal of Chemistry

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Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 49B

NUMBER 5

May 2010

CONTENTS

Papers

 

 

 

547

An efficient synthesis of some substituted piperidin-4-one thiosemicarbazone derivatives as potential anticonvulsant under microwave irradiation

 

The application of microwave technique for synthesis of thiosemicarbazone derivatives of 2, 6-diaryl-3-methyl-4-piperidones with an objective to reduce reaction time and increase yield is explored. Using microwave irradiation, all the reaction could be completed in very short duration (4-7 min) with considerable increase in the yields (53.2-80.8%). All the synthesized compounds are evaluated for their anticonvulsant activity by maximal electroshock method. Compounds 1b, 3b and 6b have been found to exhibit excellent anticonvulsant activity.

 

 

 

 

Sameer Rastogi & Harshita Rastogi

 

Department of Pharmacy, Sunder Deep Pharmacy College, NH-24, Sunder Deep Nagar, Dasna, Ghaziabad 201 001 India

 

 

 

 

 

 

 

554

QSAR studies of imidazo(1,5-a)quinoxalines amides, carbamates and ureas as potent GABA modulators

 

Quantitative structure activity relationship (QSAR) studies have been performed on imidazo(1,5-a)quinoxalines amides, carbamates and ureas. The QSAR models have been developed by using multiple linear regression in order to identify descriptors, which are actually focusing towards the biological activity. Using this model novel anxiolytics and anticonvulsants can be obtained with improved potency and pharmacokinetic profile.

 

 

Sarvesh Kumar Paliwal, Supriya Singh, Shikha Kumari, Anees A Siddiqui &  Shailendra Kumar Paliwal

 

Department of Pharmacy, Banasthali University, Rajasthan, India

 

 

 

 

 

 

 

 

 

 

 

 

 

561

Synthesis and semiempirical studies of quino­dimethane derivatives as precursors for indigoid dyes

 

Reaction of cyclohexan-1,4-dione with different active methylene heterocycles afforded tetrahydroquinodimethane derivatives, in moderate to good yield.  p-Quinodimethane derivatives, which may act as chromophores in indigoid dyes, can be obtained by dehydrogenation of tetrahydroquino­dimethane derivatives with an excess of DDQ in refluxing chlorobenzene.

 

 

 

 

 

R T Pardasani, Pushpa Pardasani & Ignatious Abraham

 

Department of Chemistry, University of Rajasthan, Jaipur 302 055, India

 

 

 

 

 

 

 

565

Studies on phosphine free Pd-salen complexes as effective catalysts for aqueous Suzuki reaction

 

Palladium complexes of the salen ligands, N,N'- bis(salicylidene)-ethylenediamine and N,N'-bis(salicylidene)-1,2-phenylenediamine have been synthesized and explored for their catalytic activity in phosphine-free aqueous Suzuki reaction. Rapid transformation of substituted aryl iodides and aryl bromides into corresponding biaryls has been observed with excellent yield ranging from 70-86%, under optimized conditions.

 

 

 

Sanjay R Borhade & Suresh B Waghmode*

 

Department of Chemistry, University of Pune, Ganeshkhind, Pune 411 007, India

 

 

 

 

 

 

 

573

Titanocene(III) chloride mediated reductive cleavage of arylcyclopropyl ketones

 

 

 

 

M Paira, S K Mandal & S C Roy

 

Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700 032, India

 

 

 

 

 

 

 

 

 

 

578

Synthesis and in vitro study of biological activity of heterocyclic N-Mannich bases of 3,4-dihydro­pyrimidine-2(1H)-thiones

 

Four series of N-Mannich bases of 3,4-dihydropyrimidine-2(1H)-thiones (DHPMs) 7a-g, 8a-g, 9a-g and 10a-g have been prepared by Mannich reaction of four DHPMs derivatives 4a, 4b, 4c and 4d respectively with seven different heterocyclic secondary amino compounds 6a-g and formaldehyde 5. All the four series of N-Mannich bases have been analyzed with a view to elucidate their elemental analysis and spectral studies (FTIR, 1H NMR). They have been assayed in vitro for their antimicrobial activity.

 

 

 

 

T B Shah, A Gupte, M R Patel, V S Chaudhari , H Patel & V C Patel

 

Department of Chemistry, Sardar Patel University,  Vallabh Vidyanagar 388 120, India

 

 

Notes

 

 

 

587

A facile four component one-pot synthesis of poly­hydroquinoline derivatives catalyzed by ionic liquid via modified Hantzsch reaction

 

An efficient and newer Hantzsch reaction for the synthesis of polyhydroquinoline derivatives have been reported via four-component condensation of aldehydes, cyclic 1,3-diketones, b-keto esters, NH4OAc and catalytic amount of ionic liquid 1-vinyl-3-ethyl imidazolium iodide [VEim] I. This methodology is operationally simple, economical, rapid and high yielding.

 

 

 

Jay P Nirmal, Pratish V Dadhaniya, Manish P Patel & Ranjan G Patel*

 

Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, India

 

 

 

 

 

 

 

 

 

593

Efficient synthesis of some novel spiro heterocycles containing triazine nucleus and their microbiological activity

 

The compounds 4-[(2,4-substituted benzylidine)-amino]-3-thioxo-1,2,4-triazin-5-one 2 have been treated with bromine in glacial acetic acid to yield, 4-[(2,4-substituted benzylidine)-amino]-6,6-dibromo-3-thioxo-1,2,4-triazin-5-one 3. The di­bromo compound 3 has been subjected to reaction with substituted triazoles and amino thiophenol to furnish, 1-thia-2,3-(3’-substituted)-triazolo-4,6,7,9-tetraza-4,6,7-trihydro-8-thio­xo-10-oxo-9[(2"/4" substituted benzylidine)-amino] spiro [4.5] decane 4 and, 1-thia-2,3-(3'-substituted)-benzo-4,6,7,9-tetraza-4,6,7-trihydro-8-thioxo-10-oxo-9[(2"/4"-substituted benzylidine)-amino] spiro [4.5] decane 5 respectively.

 

 

 

 

 

 

 

Vijay V Dabholkar & Tripathi Dilip Ravi

 

Organic Research Laboratory, Department of Chemistry, K.C. College, Churchgate, Mumbai 400 020, India

 

 

 

 

 

 

 

598

Epoxidation studies of terpenes with urea hydrogen peroxide and phosphotungstic acid

 

Some olefinic mono- and sesquiterpenoids have been region­selectively converted to their corresponding epoxides using urea hydrogen peroxide as oxidant in the presence of dodeca-phosphotungstic acid as catalyst.

 

 

 

 

 

 

 

 

Damandeep Kaur, R Manktala, K K Chahal & B R Chhabra

 

Department of Chemistry, Punjab Agricultural University, Ludhiana 141 004, India

 

 

 

 

 

 

 

 

 

 

 

 

 

603

Synthesis of 1-aryl-4-(3-nitrophenyl­me­thylene)-6-[(1Z)-2-arylvinyl]-3H-1,3,5-triazin-2-ones

 

 

 

 

 

T Venkata Maruthi Kumar, G V Panakala Rao, V Prabhakar Reddy & P Hanumantha Rao

 

Department of Chemistry, Post Graduate College of Science, Saifabad, Osmania University, Hyderabad 500 004, India

 

 

 

 

 

 

 

606

A facile synthesis of carvedilol, β-adrenergic blocking agent, via a key 5-substituted-2-oxazolidinone intermediate

 

A facile synthesis of Carvedilol via a key 5-substituted-2-oxazolidinone intermediate is described and this approach avoids the formation of bis side product (impurity B). This approach could be useful for the preparation of many β-amino alcohols without formation of bis impurity.

 

 

 

 

G Madhusudhan, B Anand Kumar, U S Chintamani, M Narasimha Rao, D Udaykiran, T Suresh,
V Kiran Kumar & K Mukkanti

 

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

 

 

 

 

 

 

 

611

Acidic task specific ionic liquid catalyzed synthesis of dihydropyrimidinones

 

[bmim]HSO4, an acidic ionic liquid has been used as catalyst for simple, green and efficient synthesis of an array of 3,4-dihydropyrimidin-2-(1H)-ones using thermal and microwave irradiation. Products were obtained in high state of purity and good yields using this one pot methodology.

 

 

 

 

Vasundhara Singh, Sukhbir Kaur, Rajni Ratti, Goverdhan L Kad & Jasvinder Singh

 

Department of Applied Sciences, PEC University of Technology, Chandigarh 160 012, India

 

 

 

 

 

 

 

 

 

 

 

 

 

617

ZrCl4 catalyzed efficient one-pot synthesis of novel methylene-bis-β-amino/methylene-bis-β-acetamido ketones

 

Zirconium(IV)chloride (ZrCl4) catalyzed efficient one-pot synthesis of methylene-bis-β-amino/methylene-bis-β-aceta­mido ketones at room temperature has been described. In the presence of ZrCl4, the three-component Mannich-type reaction via a variety of insitu generated aldimines with various ketones, methylene-bis-methoxybenzaldehyde and aromatic amines in ethanol, led to the formation of methyl­ene-bis-β-amino ketones 4a-j and the four-component Mannich-type reaction of methylene-bis-methoxy­benzalde­hyde with ketones, acetonitrile and acetyl chloride resulted in the corresponding methylene-bis-β-acetamido ketones 5a-f in high to excellent yields. All the newly synthesized compounds have been characterized by their spectral and elemental analyses.

 

 

 

Ch Sanjeeva Reddy, A Nagaraj, A Srinivas & G Purnachandra Reddy

 

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

 

 

 

 

 

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