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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

VOLUME 43 B

NUMBER 6

JUNE 2004

 

 

CONTENTS

 

 

Rapid Communications

1263

 

 

 

 

 

A total synthesis of 4-hydroxynimesulide

 

IPC: Int.Cl.7 A 61 K 31/04

 

 

 

4-Hydroxynimesulide 1, a unique metabolite of Nimesulide has been synthesized by the formation of 4-methoxynimesulide and its subsequent demethylation with aq. HBr-AcOH/anhyd. AICI3-CH2CI2.

Parmjeet Singh, Amarjit Singh &

G C Sharma*

Papers

 

1265

 

 

 

Enantiospecific total syntheses of

(–)-valeranone

 

IPC: Int.Cl.7 C 07 C 13/38

Three methods have been developed for the enantiospecific total synthesis of the sesquiterpene (–)-valeranone.

 

 

 

A Srikrishna*, R Viswajanani & C Dinesh

 

1275

 

 

 

 

Ceric ammonium nitrate (CAN) catalyzed Baeyer-Villiger oxidation of carbonyl compounds, specially 20-oxosteroids

 

IPC: Int.Cl.7 C 07 K 1/00

The role of ceric ammonium nitrate (CAN) as an effective catalyst in the peracid induced Baeyer-Villiger oxidation of carbonyl compounds with special reference to steroids has been demonstrated.

 

 

 

Papori Goswami, Saroj Hazarika,

Archana M Das & Pritish Chowdhury*

 

1282

 

 

 

 

 

 

Synthesis of Nα-protected peptide acids by the N→C chain extension employing O,N-bis-trimethylsilyl-amino acids using the mixed anhydride method

 

IPC: Int.Cl.7 C 07 K 1/00

 

 

Synthesis of Nα-protected peptide acids employing N→C extension strategy using in situ generated X-NH-CHR'-CO-O-CO-iBu and O, N-bis-trimethysilyl-amino acids has been accomplished. The method has been extended to the synthesis of the known a-helical peptide fragment H-Val-Ala-Leu-Val-Ala-Leu-OH.

 

 

Subramanyam J Tantry &

Vommina V Suresh Babu*

 

1288

 

 

 

 

A rapid and convenient synthesis of α and β forms of acetylated derivatives of sugars under microwave irradiation

 

IPC: Int.Cl.7 C 07 H

The synthesis of α and β forms of penta as well as octa acetyl derivatives of several sugars under microwave irradiation with improved yields is described.

 

 

 

Basanagoud S Patil &

Vommina V Suresh Babu

 

1292

 

 

 

 

 

Alkyl esters of 6-methoxy-2-naphthylacetic acid as potential prodrugs — Synthesis, physicochemical properties, chemical stability and enzymatic hydrolysis

 

IPC: Int.Cl.7 C 07 C 63/00

Alkyl esters of 6-methoxy-2-naphthylacetic acid as potential prodrugs — Synthesis, physicochemical properties, chemical stability and enzymatic hydrolysis.

 

 

 

 

 

Lalit Kumar Wadhwa,

Senthil Kumar Chandiran &

Pritam Dev Sharma*

 

1299

 

 

 

 

 

Alkylation of substituted benzaldehyde on a solid matrix by using Grignard reagent

 

IPC: Int.Cl.7 C 07 C 47/542

 

Alkylation of aromatic aldehydes by using Grignard reagent on silica matrix yields pure substituted benzyl alcohols.

 

 

 

 

 

Sabita Patel, Mamata P Panda,

Minati Kuanar & B K Mishra*

 

1302

 

 

 

 

 

 

 

Synthesis and biological activity of some isoniazid based 1,3,4-oxadiazole derivatives

 

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

 

M S Y Khan*, Gita Chawla & M Asad Mueed

Isoniazid and 1,3,4-oxadiazole are important moieties because of their highly significant biological actions. In the present studies, isoniazid has been used as the starting material for synthesising different oxadiazoles. These compounds have been screened for their antiinflammatory and antibacterial properties.

1306

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Synthesis and biological evaluation of 7-N-(n-alkoxyphthalimido)-2-hydroxy-4-aryl-6-aryl­iminothiazolidino [2,3-b] pyrimidines and related compounds

 

IPC: Int.Cl.7 C 07 D//A 61 P 31/04, 31/10, A 61 P 33/06

 

 

 

 

 

 

 

 

 

 

 

 

Substituted aryl thioureas 1a-c react with chloroacetic acid in the presence of anhydrous sodium acetate to furnish 2-aryliminothiazolidin-4-ones 2a-c. Condensation of w-bromo-alkoxyphthalimides 3a-c with 2a-c give the corresponding alkoxy-phthalimide derivatives of 2-aryliminothiazolidin-4-ones 4a-i. These on condensation with araldehydes 5a-c give 3-N-(alkoxy-phthalimido)-5-arylidene-2-arylimino-thiazolidin-4-ones 7a-a¢. In an alternative route 5a-c react with 2a-c to give 6a-i, which could be cyclised with urea in the presence of sodium acetate to yield the corresponding thiazolidinopyrimidine 8a-i. 7a-a¢ are also prepared from 6a-i with 3a-c, which give final compounds 9a-a¢ on cyclisation. Alternatively, 8a-i when condensed with 3a-c also furnish the compounds 9a-a¢. Evaluation of antimalarial and antibacterial activity is also reported.

 

 

Bhawani Singh, Deepika Mehta,

Lalit K Baregama & G L Talesara*

 

1314

 

 

 

 

 

 

 

 

 

 

Synthesis and antimicrobial activity of new polyfunctionally substituted pyridines and their fused derivatives

 

IPC: Int.Cl.7 211/00, 213/00, A 61 P 31/04, 31/10

 

 

 

 

 

Ethyl pyruvate (EP) on reacting with malononitrile or isothiocyanates gives the pyridine derivatives 5 and 9a,b, respectively. Chalcone derivative of EP reacts with malononitrile to yield the pyran derivative which in turn is transformed into pyridine derivative 14. Reactivity of 5 and 9a towards different organic reagents has been investigated. Antimicrobial activity for some of the newly synthesized pyridines is also reported.

 

 

 

Bhawani Singh, Deepika Mehta,

Lalit K Baregama & G L Talesara*

 

1320

 

 

 

 

 

 

 

A comprehensive electrochemical studies on some synthesized substituted 3-arylazo-2,4,6-trimethylquinolines

 

 

 

IPC: Int.Cl.7 C 07 D 215/00

 

The electrochemical reduction of synthesized 3-arylazo-2,4,6-trimethylquinoline has been studied over wide pH range. The kinetic parameters have been calculated. A plausible mechanism has also been suggested on the basis of d.c. polarography, cyclic voltammetry, control potential, electrolysis and product identification.

 

 

Pratibha Sharma*, Ashok Kumar,

Priti Pandey & Nilesh Rane

 

1329

 

 

 

 

 

 

 

 

 

A new oxygenated tricyclic sesquiterpene from a soft coral of Nephthea species of Andaman and Nicobar coasts of Indian ocean

 

IPC: Int.Cl.7 C 07 D 311/30

 

 

 

 

A new oxygenated tricyclic sesquiterpene,1a-hydroxy (+)-cyclocolorenone 2 has been isolated from a soft coral of Nephthea species from Andaman and Nicobar coasts of Indian ocean, together with the known oxygenated tricyclic sesquiterpene, (+)-cyclo­colore­none 1 and their structures are deduced by using high resolution spectral data.

 

 

 

Ch Bheemasankara Rao, V Chandra Sekhar, B Sarvani & D Venkata Rao*

 

1332

 

 

 

 

 

 

Flavones from Elsholtzia stauntonii

 

IPC: Int.Cl.7 C 07 D 311/30

 

 

 

 

Structures of two new flavones isolated from Elsholtzia stauntonii Benth have been determined by spectroscopic methods as 5-hydroxy-7,5¢-dimethoxy-6,8-dimethyl-3¢,4¢-methylenedioxyflavone 1 and 5-hydroxy-7-methoxy-8-methyl-5¢-(3¢-methyl-but-2-enyl)-3¢,4¢-methylenedioxy­flavone 2.

 

 

 

Shuhe Kang*, Yanbin Wang Li Li &

Shangzhen Zheng

 

 

 
NOTES

 

1335

 

 

 

 

 

A simple, efficient and regioselective oxy­chlori­na­tion of aromatic compounds using ammonium chloride and oxone®

 

IPC: Int.Cl.7 C 07 C 15/00

An efficient, mild and regioselective method for the oxychlorination of aromatic compounds is reported using ammonium chloride and oxone® for the first time.

 

 

 

 

N Narender, K V V Krishna Mohan,

P Srinivasu, S J Kulkarni* & K V Raghavan

 

1339

 

 

 

 

Regio-specific ring opening of terpene and aryl-substituted epoxides with Br2/DMS reagent

 

IPC: Int.Cl.7 C 07 C 13/18

 

 

 

B K Bettadaiah & P Srinivas*

 

1341

 

 

 

 

 

 

Facile synthesis of 2-arylbenzo[b]furans through unusual acid catalysed 1,2-elimination

 

IPC: Int.Cl.7 C 07 D 307/78

 

 

2-Arylbenzo[b]furans have been synthesized in good to excellent yields through unusual acid catalysed 1, 2-elimination of 2-aroyl-2-aryl-3-hydroxybenzo[b]furans isolated as an intermediate for the first time. Their structures have been confirmed by X-ray crystallography.

 

 

Ashok K Jha, Pushkar C Sharma,

Prakas R Maulik,Umesh Yadav & K Hajela

 

1345

 

 

 

 

Facile synthesis of novel fluorescence active 12H-benzo[e]indolo[3,2-b]benzofuran and its derivatives

 

IPC: Int.Cl.7 C 07 D 307/78

 

 

 

A V Karnik* & S P Upadhyay

 

1349

 

 

 

 

 

A new process for the production of tri­methyl­hydroquinone

 

IPC: Int.Cl.7 C 07 C 50/00

 

 

To reduce the pollution and to decrease synthesis steps, a new process has been developed. It is direct hydroxylation of 2,3,6-trimethylphenol with H2O2 over copper hydroxyphosphate. The results are very significant.

 

 

H Zhu* & S Y Chen

 

1355

 

 

 

 

 

 

A convenient synthesis of some novel pyrazole derivatives

 

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

 

 

 

Synthesis of some novel pyrazole derivatives is achieved by condensation of pyrazole-4-carbaldehydes 1a,b with different reagents as acylglycine, benzamidine hydrochloride, ethyl azidoacetate, malononitrile and cyclohexanone.

 

 

 

El-Saied A Aly*, Mohamed A El-Borai &
Mohamed A Barren

 

1360

 

 

 

 

 

Tetra-n-alkyl ammonium bromates as a primary oxidants in the oxidation of alcohols to carbonyl compounds

 

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

 

Tetra-n-alkylammonium bromates are prepared by a simple procedure from the corresponding bromides and used as primary oxidants for the oxidation of alcohols to the carbonyl compounds. Reaction conditions are simple and products are obtained in high yield.

 

 

Dibakar Deb, Satya Sandhya Das,

Utpal Nath & Pranab J Das *

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.7: International Classification 7th edition, 1999