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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

VOLUME 43B

NUMBER 2

FEBRUARY 2004

 

 

CONTENTS

 

 

Rapid Communications

357

Monohalogenation (bromination and iodina­tion) of electron rich arenes by tetra­-alkyl­ammoniumhalides in presence of conc.
2­SO
4

 

IPC: Int.Cl.7 C 07 C 17/00

Arenes undergo electrophilic substitution reaction when treated with tetraalkylammonium halides (bromides and iodides) in presence of conc. H­2­SO4 to give p-haloarenes in high yields.

 

 

 

 

Yi Yi Myint & M A Pasha*

Papers

361

Synthesis, characterisation of new chromano­isoxazoles and investigation of optical power limiting properties

IPC: Int.Cl.7 C 07 D 261/02

 

 

 

 

Y L N Murthy*, R Surya Prabha & Seetharam Shettigar

 

 

 

367

Simple and efficient synthetic routes to s-triazinyl dithiocarbamte derivatives: 2,4-Di-arylamino-6-[N-(4˘-ethoxyphenyl)dithio­car­b­a­moyl]-s-triazines and 2,4-bis-[N-(4˘-ethoxy- phenyl)dithiocarbamoyl]-6-arylamino -s-tria­zines

IPC: Int.Cl.C 07 D 251/12, C 07 C 333/00

Compounds 4a-f and 7a-f have been synthesized by two different methods. 4a-f and 7a-f have been screened for antimicrobial activity. The products display moderate to good activity.

 

 

R M Desai, N R Ravat & V H Shah*

 

 

 

374

Kinetics and mechanism of in situ bromohydroxylation of cinnamic acids by sodium bromate – sodium bisulphite reagent in aqueous acetonitrile medium

IPC: Int.Cl.7 C 07 C 57/44

 

 

 

 

 

J Viroopakshappa & V Jagannadham*

 

 

 

 

 

 

378

A facile synthesis of novel nitrogen-sulphur heterocycles containing the amidino moiety and their antimicrobial activity ľ Part I

IPC: Int.Cl.7 C 07 D 285/01 

// A 61 P 31/04, 06

The interaction of amidinothiocarbamide 1 and 4 - bromo- 1,3 - substituted-pyrazol-5-ones 2 afford 2-guanidino-4, 6-substituted-pyrazolo [5,4-d]thiazoles 5 which on treatment with aldehydes yield the corresponding schiff's bases 6. The corresponding schiff’s bases  6 are also obtained by an alternate unambiguous one step synthesis. Similarly, the reaction of 1 with diethyl bromomalonate to afford fused ring heterocycles has been studied in detail. Certain compounds synthesized exhibit antimicrobial and antitubercular activity.

 

 

Madhukar S Chande* & Peter V R Carvalho

 

385

Bisheterocyclic synthesis and antimicrobial studies on some biologically significant 2-[N-(3˘-chloro-4˘-substituted azetidinone-2)]­ami­no-4-hydroxypurines

IPC: Int.Cl.7 C 07 D 473/00 // A61 P 31/04

2,5,6-Triamino-4-hydroxypyrimidine 1 reacts with formic acid at very high temperature, followed by diazotization and coupling with b-diketones to yield 3a-h which on subsequent treatment with chloroacetyl chloride in the presence of triethylamine and 1,4-dioxane result in the formation of a novel series of bis-heterocyclic system
4a-h. Their structures have been confirmed by IR, NMR, mass and elemental analysis data. Synthesized compounds have been tested for their antimicrobial activities.

 

 

Pratibha Sharma*, Ashok Kumar & Shikha Sharma

 

 

 

 

 

389

Synthesis and biological activities of novel 2-(5˘-substituted-3˘-phenylindole-2˘-yl)-1, 3, 4-oxadiazino[5,6-b]indole and 3-(5˘-substituted-3˘-phenylindole-2˘-amido)spiro-(indol-3˘˘,2-thiazolidine)-2˘˘,4-diones

IPC: Int.Cl.7 C 07 D 209/04 

 

// A 61 P 31/04, 33/10, 1/06 

 

The title compounds have been synthesized from 5-substituted-3-phenylindole-2-carbohydrazides and isatin and tested for their biological activities (antibacterial, antifungal, anthelmintic and anticonvulsant).

 

J S Biradar* & S Y Manjunath

 

393

Synthesis and biological activity of some 3-methyl/ethoxycarbonyl-6-arylimidazo[2,1-b]­thiazoles and their 5-bromo/5-formyl deri­vatives

IPC: Int.Cl.7 C 07 D 277/00

// A 61 P 31/04, 10, 33/10, 25/08

Effect of 4-substituent of 2-amino-4-methyl/ethoxy­carbonyl­thiazole is discussed during the condensation with arylacyl bromide to afford 3-methyl/ethoxy carbonyl-6-arylim­Iidazo[2,1-b]thiazoles 8/9.

 

 

 

 

I M Khazi*, R S Koti, A K Gadad, C S Mahajanshetti, Y B Shivakumar & M V Akki

 

399

Synthesis and biological activity of 4-oxothiazolidines and their 5-arylidenes

IPC: Int.Cl.7 C 07 D 277/00

// A 61 P 31/04, 33/10, 1/06

A series of 5-arylidene-2-aryl-3-[(2-benzothiazolylthio)-acetamidyl]-1,3-thiazolidin-4-ones (4, 5) have been synthesised by appropriate methods. All the compounds have been screened for their anti-fungal, anti-inflammatory and anthelmintic activities. The structures of the synthesised compounds (4 and 5) have been established on the basis of their elemental analyses and spectral data.

 

 

 

 

 

S K Srivastava* & R Yadav & S D Srivastava

 

 

 

 

 

406

Isoechinatine, a pyrrolizidine alkaloid from Cynoglossum furcatum

IPC: Int.Cl.7 C 07D 209/00

The pyrrolizidine alkaloids isoechinatine 1, echinatine, neocoramandaline heliotridine 3-hydroxy-6-methyl­pyri­dine of Cynoglossum furcatum have been isolated and characterized.

 

 

Text Box: 1

 

 

R Ravikumar & A J Lakshmanan*

 

Notes

410

Stereoselective synthesis of steroidal (3R)-spiro-D2 ˘ -1˘,3˘,4˘-oxadiazoline

IPC: Int.Cl.7 C 07 D 271/12, J 1/00

Condensation of steroidal ketone 1 with semicarbazide hydrochloride yields steroidal semicarbazone 2 and reaction of steroidal semicarbazone 2 with acetic anhydride and pyridine at 80°C affords steroidal (3R)-spiro-D˘-1˘,3˘,4˘-oxadiazoline 3.

 

 

 

Shamsuzzaman*, Nazish Siddiqui & Anwar Salim

 

413

One-pot syntheses of heterocycles containing 1,4-thiazine nucleus

IPC: Int.Cl.7 C 07 D 279/10

 

 

 

 

Rajni Gupta, Vibha Shrivastava, Archana Gupta, P S  Verma & R R Gupta*

 

 

 

 

 

 

 

417

One pot synthesis of 3-(1H-imidazo[4,5-f]qui­no­lin-2-yl)-chromen-2-one under micro­wave irradiation

IPC: Int.Cl.7 C 07 D 215/00, 235/00

 

 

 

3a-f

 

B Rajitha*, M Kanakalingeswara Rao & P Narsimha Reddy

 

420

Microwave assisted phase transfer catalysis: An efficient solvent free method for the synthesis of cyclopropane derivatives

IPC: Int.Cl.7 C 07 C 13/02

Microwave assisted solvent free synthesis of various cyclopropane derivatives 2a-e starting from active methylene compounds 1a-e and 1, 2-dibromoethane under phase transfer conditions is described.

 

 

 

V K Gumaste, Asgar J Khan, B M Bhawal & A R A S Deshmukh*

 

423

Ecofriendly synthesis of quinazolin-4(3H)-ones

IPC: Int.Cl.7 C 07 D 215/00

Quinazolin-4(3H)-ones have been synthesized under neat reaction condition in the presence of DCC as a condensing agent using microwave irradiation.

 

 

 

Mazaahir Kidwai*, Ruby & Shweta Rastogi

 

 

 

 

 

426

Oxidation of benzylic bromides by DMSO in the presence of zinc salts: A new variant of Kornblum's method

IPC: Int.Cl.7 C 07 C 25/00

Besides standardizing the oxidation conditions, formation of the corresponding alcohol and S-methyl ether as minor products in the reaction is mechanistically explained.

 

 

 

 

K Subrahmanya Bhat, S Srinivas, P Srinivas & K N  Gurudutt*

 

430

Sulfuric acid adsorbed on silica gel and chromium(VI) oxide: Rapid and selective oxida­tion of alcohol in solvent-free condition

IPC: Int.Cl.7 C 07 B 33/00

A rapid and selective method for the oxidation of alcohols to carbonyl compounds that occurs on silica gel-sulfuric acid supported CrO3 in solventless system.

 

 

 

 

Majid M. Heravi*, Nasrin Farhangi, Yahya Sh Beheshtiha, Mitra Ghassemzadeh & Koroush Tabar-Hydar

 

432

Reduction of polyfunctional aromatic nitro compounds using lithium aluminium hydride

IPC: Int.Cl.7 C 07 B 31/00

A variety of aromatic bifunctional compounds, N-(nitrophenyl)benzamides 1a-c, nitrobenzanilides 1d-f, 2,2˘-dinitrodiphenyl amine 5a, (bis-2-nitro­anilino)­me­thane 5b, 2,2˘-dinitrodiphenylether 5c, 2-nitrophenyl-2˘-nitrophenoxymethane 5d, 1,3-dinitrobenzene 6a, 2-nitrobenzaldoxime 6b, 2-N-(2˘-nitrophenylmethyl)amino benzoic acid 6c, 2-nitrophenoxymethyl phenyl ketone 6d are reduced using lithium aluminmium hydride. Nitro group is found reluctant towards reduction in some cases whereas in others, it is reduced in to different extents.

 

M M Joseph & Dominic E Jacob*

 

437

The use of basic resin in the preparation of tetrahydropyranyl derivatives of alcohols and phenols

IPC: Int.Cl.7 C 07 D 309/00

A quick and efficient method for the preparation of tetrahydropyranyl (THP) derivatives of phenols and alcohols using a basic resin IRA-400 (iodide) is described.

 

 

Devdutt Chaturvedi, Atul Kumar & S Ray*

 

 

 

 

 

439

Synthesis and evaluation of some substituted mercaptothiazoles and their derivatives of biological interest

IPC: Int.Cl.7 C 07 D 279/00, 277/72

// A 61 P 31/04

The title compounds have been synthesized from 4-(4'-chlorophenyl)-D4-thiazoline-2-thione, which in turn is synthesized by the reaction of p-chlorophenacyl bromide with ammonium dithiocarbamate.

 

 

 

Shashikant R Pattan*, Talath Sirajunisa &
 Jayashri Pattan

 

 

 

 

442

Lipid constituents from Centratherum anthelminticum (seeds)

IPC: Int.Cl.7 A 61 K 35/78

 Six new aliphatic compounds and a sterol have been isolated and characterized as hexatetracontane-16-ol 1, 6,9-icosadiene 2, butyl-11-hydroxyoctadecanoate 3, hexyl-3-hydroxynonanoate 4, hexyl-9-hydroxyheptatria­contanoate 5, heptadecylnonadecanoate  6 and (24a/S)-stigmasta-5,22-diene- 3b-ol 7, by spectral and chemical means.

 

Manjul Verma, Shrilakshmi Deshiraju,
Mustazi Jafri & B K Mehta*

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

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