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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

 

VOLUME 43 B

NUMBER 10

OCTOBER  2004

 

 

CONTENTS

 

 

2147

 

 

 

 

 

 

 

 

 

Synthesis and NMR study of the stereochemistry of r(2),c(6)-diaryl-c(3)-chloropiperidin-4-ones

 

IPC: Int.Cl.7 C 07 D 295/00

 

 

 

 

 

 

 

r(2),c(6)-Diaryl-c(3)-chloropiperidin-4-ones are obtained by the epimerization of r(2),c(6)-diaryl-t(3)-chloropiperidin-4-ones by treatment with ammonia in DMF. The 1H and 13C NMR spectra of these piperidones are measured in CDCl3 at 360 and 90 MHz respectively and the chemical shifts assigned unambiguously employing one dimensional 1H and 13C and two-dimensional H,H-COSY, C,H-COSY and NOESY NMR spectra. NMR spectroscopic parameters of the epimeric pair of chloropiperidones have been compared and the differences rationalized in terms of stereochemical features.

 

 

 

S Perumal*, V Manonmani, V Vijayabaskar, S Selvaraj & A Lycka

 

2152

 

 

 

 

 

Homologation of a-amino acids to b-amino acids : 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Na-protected aminoacyldiazomethanes

 

IPC: Int.Cl.7 C 07 C 229/00

 

An efficient and stereospecific homologation of urethane protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of urethane protected amino acid and 9-fluorenylmethyl chloroformate for acylation of diazomethane and converted into corresponding β-amino acids using microwave irradiation.

 

Kantharaju & Vommina V Suresh Babu*

2159

 

 

 

Mutual prodrugs of 4-biphenylacetic acid and phytophenolics as safer NSAIDs ¾ Synthetic and spectral studies

 

IPC: Int.Cl.7 C 07 C 57/32

Mutual prodrug approach for the development of safer NSAIDs using phytophenol/alcohol as promoieties.

 

 

Pritam Dev Sharma*, Gurbinder Kaur, Sumeet Kansal & Senthil Kumar Chandiran

2165

 

 

 

Synthesis of 1-alkyl-6-aryl-3-n-propyl-5-thio­xo/
oxo-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-d]pyri­mi­­­din-7-ones

 

IPC: Int.Cl7. C 07 D 239/00

1-Alkyl-6-aryl-3-n-propyl-5-thioxo/oxo-4,5,6,7-tetra ­hydro-1H-pyrazolo [4,3-d]pyrimidin-7-ones have been obtained from the reactions of 4-amino-1-alkyl-3-n-propylpyrazole-5-carboxamides with aryl isothio­cyanates and phenyl isocyanate.

N Ram Reddy & P Pratap Reddy*

2170

 

 

 

 

Synthesis and characterization of 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives containing 2-chloropyridin-5-yl-methyl moiety

 

IPC: Int.Cl.7 C 07 D 285/12, 271/10

A number of new compounds containing 2-chloro­pyridin-5-yl-methyl substituted 1,3,4-thia­dia­zole and 1,3,4-oxadiazoles are prepared with a view to study their insecticidal properties.

 

 

 

B Shivarama Holla*, C S Prasanna, Boja Poojary, K S Rao, K Shridhara & U Ganesha Bhat

 

2175

 

 

 

 

 

Rapid formation of acetates under microwave irradiation using montmorillonite acid clay catalyst

 

IPC: Int.Cl.7 C 07 C 49/00

 

 

 

The combination of microwave irradiation and montmorillonite [H+] clay catalyst dramatically enhances the rate of formation of acetates of alcohols, phenols and amines when treated with acetic anhydride. A series of acetates have been prepared with significantly low reaction times in very good to excellent yields.

 

 

Uppuluri V Mallavadhani*, Laxmidhar Sahoo &

Subhra Roy

2178

 

 

 

Redox behaviour of chromium(VI) towards d-mannose in the presence and absence of micelles and inorganic salts

 

IPC: Int.Cl.7 C 01 G 37/00

The redox reaction between d-mannose and chromium(VI) has been studied in aqueous as well as in the presence of SDS and TX-100 micelles at 60°C.

 

 

Kabir-ud-Din*, Abu Mohammad Azmal Morshed & Zaheer Khan

2189

 

 

 

 

Synthesis, characterization and biological activities of substituted oxadiazole, triazole, thiadiazole and 4- thiazolidinone derivatives

 

IPC: Int.Cl.7 C 07 D 271/10, 249/08, 285/12 // A 61 P 29/00, 31/04

A number of oxadiazole, triazole, thiadiazole and thiazolidinone derivatives have been synthesized and evaluated for their antiinflammatory and antibacterial activities.

 

 

Mohd Amir*, M SY Khan & M S Zaman

2195

 

 

 

 

Novel synthesis and antimicrobial investigation of pyrazolo[1, 5-a] pyrimidine and pyrazolo­triazine containing piperidinyl sulfone moiety

 

IPC: Int.Cl.7 C 07 D 239/00,

231/00 // A 61 P 31/04

Aminopyrazole 3 is synthesized and its reactivity towards some electrophilic reagents is investigated.

 

 

 

N M Saleh, Y A Ammar, J A Micky, H A S Abbas & M S A EL-Gaby*

2203

 

 

 

 

 

Activated nitriles in heterocyclic chemistry: Facile synthesis and antimicrobial activity of some pyrimidine, pyrazolopyrimidine and pyrazolotriazine derivatives containing sulfonamido moiety

 

IPC: Int.Cl.7 C 07 D 239/00,

231/00 // A 61 P 31/04

Hydrazone 2 and aminopyrazole 8a,b have been used as starting materials for the synthesis of heterocyclic compounds .

 

 

 

 

Y A Ammar, N M Saleh, J A Micky, H A S Abbas & M S A El-Gaby*

2212

 

 

 

 

Theoretical studies of the acid-catalyzed condensation of ninhydrin with aromatic compounds

 

IPC: Int.Cl.7 C 07 C 39/04, 39/08

 

Sandip Kumar Kundu, Suven Das & Animesh Pramanik*

2217

 

 

 

 

 

 

 

 

 

Phytochemical investigation of Shilajit

 

IPC: Int.Cl.7 A 61 K 35/00

 

 

 

 

 

 

 

The phytochemical investigation of Shilajit has afforded six new compounds named as shilajityl acetate, shilajitol, shilacatechol, shilaxanthone, shilanthranil and naphsilajitone along with pyrocatechol and their stereostructures have been elucidated correspondingly as 4a, 5a, 6a-trihydroxygeranyl acetate, 6-(9, 9-dimethylbutyl) phenol, 1-cyclohexyl-3, 4-dihydroxybenzene, 2, 3, 12, 13-tetrahydroxy-10, 15-[a,f]`-phenylxanth- 17-one, 2, 3, 13, 14-tetrahydroxy-15, 16-[a,f]-phenyl-7H-anthracen-18-one and 3-hydroxynaphthalenyl-6,7-g-lactone on the basis of chemical data analyses and chemical reactions.

M Ali*, I Sahrawat & O Singh

2223

 

 

 

 

Phytochemical investigation of Gomphrena globosa aerial parts

 

IPC: Int.Cl.7 A 61 K 35/00

 

Saponin 1 and triterpenoid 2 have been isolated from G.globosa along with b-sitosterol-b-d-glucoside and 1-triacontanol and their structures are elucidated by spectroscopic and chemical methods.

 

Biswanath Dinda*, Biplab Ghosh, Shiho Arima,, Nariko Sato & Yoshihiro Harigaya

Notes

2228

 

 

 

 

Synthesis of some 3-phenyl-4-methyl-6-(6-arylpyridin-2-yl)- and 3-phenyl-4-methyl-6-(4,6-diarylpyridin-2-yl) coumarins

 

IPC: Int.Cl.7 C 07 D 311/00

 

Various 3-phenyl-4-methyl-6-(6-arylpyridin-2-yl) cou­marins 5a-f and 3-phenyl-4-methyl-6-(4,6-diaryl­pyridin-2-yl) coumarins 7a-f have been synthesized by reacting 3-phenyl-4-methyl-6-coumarinoyl methyl pyridinium bromide 3 with Mannich bases 4a-f and a,b-unsaturated ketones 6a-f respectively under Kroehnke’s reaction condition.

D I Brahmbhatt*, C N Patel, V P Pandya & M A Patel

 

2231

 

 

 

 

Synthesis of some new 1,2,3-selenadia­zolo­[4',5':5,4]cyclo­pent[b]indoles and 6,11-dihydro-5-methylquino­lino­[2',3' : 5,4]cyclopent[b]indoles

 

IPC: Int.Cl.7 C 07 D 209/04

Synthesis of 4,8-dihydro-1,2,3-selenadia­ zolo­[4¢,5¢:4,5]­­cyclo­pent[b]indoles, 6,11-dihydro-5-methyl­quino­lino­[2¢,3¢:5,4]cyclopent[b]indoles and 12-methyl-6-(1¢)­pro­pen-2¢-ol)dibenzo[b,f[1,5]diazocine.

 

                                                                          3                                         5                                           6

 

 

V Sangeetha & K J Rajendra Prasad*

2235

 

 

Comparative study of Heck reaction under thermal and microwave conditions

 

IPC: Int.Cl.7 C 07 C 69/56

Comparative study of Heck reaction of various substrates under thermal and microwave irradiation reveals advantage of microwave synthesis.

 

S B Solabannavar, Uday V Desai & R B Mane*

2238

 

 

 

1,3-Dipolar cycloaddition of dipolar reagents to bischalcones in the presence of chloramine-T

 

IPC: Int.Cl.7 C 07 D 261/00, 231/00

 

Bis-pyrazolines and bis-isoxazolines are prepared by the reaction of bis-chalcones with araldehyde phenyl­hydrazones and araldoximes in the presence of chloramine-T.

 

 

V Padmavathi*, K Venugopal Reddy, M Rajagopala Sarma, R P Sumathi &  D Bhaskar Reddy

 

2243

 

 

Reduction of nitrophenols by zinc and ammonium chloride in aqueous medium

 

IPC: Int.Cl.7 C 07 C 205/20

A simple reduction procedure involving zinc and ammonium chloride in aqueous medium has been employed for the reduction of nitrophenols to aminophenols.

 

1                                                                 2

 

 

V Sridharan, M Karpagavalli,  S Muthusubramanian* & S Sivasubramanian

 

2245

 

 

 

 

Benzophenone and methylene blue sensitized photooxidation of piperine : A comparative study of photooxidation of piperine by ground state and singlet oxygen

 

IPC: Int.Cl.7 C 07 C 49/00

Photooxidation of piperine with ground state and singlet oxygen has been studied and different products 2 and 3 respectively have been obtained.

 

 

Shubha Jain*, Rajbala Pandey & Meena Chourey

2249

 

 

QSAR analysis of 2,2-dimethyl-4,5-diarylfuran-3(2H)-ones as selective cyclooxygenase-2 inhibitors

 

IPC: Int.Cl.7 C 07 D 307/00

QSAR analysis has been performed on a series of 2,2-dimethyl 4,5-diarylfuran-3(2H)-nones in order to explore the structural insights for selective cyclooxygenase-2 inhibition.

S Prasanna, E Manivannan & S C Chaturvedi*

2254

 

 

 

Some 1,4-benzoxazino[2,3-b]phenoxazines deri­vatives as antibacterial, muscle relaxant and hypnotic agents

 

IPC: Int. Cl.7 C 07 D 265/34  // A 61 P 31/04

1,4-Benzoxazino [2,3-b] phenoxazines are synthe­sised by condensation of substituted anilines with halobenzoquinones followed by cyclisation. These compounds are secreened for their antibacterial, muscle relaxant and hypnotic activities.

K G OJha*, S P Mathur, A K Mathur,

A S Chittoria, H Tahiliani & R K Sharma

2258

 

 

Isolation and characterization of anthraquinones from the stem bark of Cassia siamea

 

IPC: Int.Cl.7 C 07 C 50/18

Anthraquinone chrysophanol 1 and bianthraquinone cassiamin 2 have been isolated from the stem bark of Cassia  siamea  and  their   structures   are  elucidated  by  spectral studies.

1                                                                   2

 

Lalita Ledwani & Mukhtar Singh*

 

Authors for correspondence are indicated by (*)

                                       

                                        IPC: International Patent Classification

                                        Int. Cl.: International Classification 7 edition, 1999