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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

 

VOLUME 44 B

NUMBER 3

MARCH 2005

 

 

CONTENTS

 

Papers

 

 

 

549

Formation of mono- and di-amide- derivatives from the reaction of p-tert-butyl-calix[4]arene and a-chloro-N,N-diethylacetamide in the pre­sence of sodium hydride

 

IPC: Int.Cl.7 C 07 C 15/20

2, R1 = -OCH2CON(Et)2, R2=R3=R4=H

3, R1 = R2= -OCH2CON(Et)2, R3=R4=H

4, R1 = R3= -OCH2CON(Et)2, R2=R4=H 

 

Amjad Ali & Chebrolu P Rao*

 

 

 

 

 

 

 

553

A chiral pool based synthetic strategy for
g-hydroxyalkyl-D2-butenolides

 IPC: Int.Cl.7 C 07 D 307/26

A new stereoselective synthetic route to a g-hydroxy­alkyl-D2-butenolide has been described starting from the a-hydroxy acid chiral pool.

 

 

Saumitra Sengupta* & Somnath Mondal

 

 

 

 

 

 

 

557

Enantioselective synthesis of (S)-a-arylpropionic acids via Pd-catalyzed kinetic resolution of benzylic alcohols

 IPC: Int.Cl.7 C 07 C 53/122

A new and concise synthesis of (S)-a-arylpropionic acids is described involving Pd-catalyzed kinetic resolution of benzylic alcohols as a key step.

 

 

 

Vinay V Thakur & A Sudalai*

 

 

 

 

 

 

 

 

563

Synthesis of imidazole, coumarin and isoxazole containing new triheterocyclic compounds and their derivatives

 

 

IPC: Int.Cl.7 C 07 D 261/00, 233/54, 311/10

Reaction of substituted 4-amino-3-methyl-5-styryl­isoxazoles 1 with 3-(2-bromoacetyl)coumarin 2 in abs. ethanol leads to the formation of 3-[2-(3-methyl-5-styryl-4-yl amino)acetyl]chromen-2-ones 3, which are subsequently cyclised by treatment with KSCN to 3-[1-(3-methyl-5-styryl-isoxazol-4-yl)-2-mercapto-1H-imidazol-4-yl]-1-benzopyran-2H-ones 4. 2-Mercapto­imidazoles 4 on treatment with ClCH2COCl in DMF / abs. ethanol give unexpected product esters 5. The reaction of 4 with phenacyl bromides results in the formation of thioethers 6.

 

 

 

E Rajanarendar*, D Karunakar & M Srinivas

 

 

 

 

 

 

 

568

Reactions of amidines with some carboxylic acid hydrazides

 IPC: Int.Cl.7 C 07 D 249/08

Ten amidrazone derivatives and twelve 1,2,4-triazole derivatives have been synthesized and their structures are established by elemental analysis, IR and 1H NMR spectral data.

 

 

 

Şule Bahçeci, Haydar Yükse* & Mevlut Serdar

 

 

 

 

 

 

 

573

Facile ring opening of 2-aryl[1,3,4]­oxa­di­a­zino[5,6-b]quinoxalines with sodium alkoxides

 IPC: Int.Cl.7 C 07 D 215/00

Reaction of 2,3-dichloroquinoxaline 1  with acid hydrazides 2 gives oxadiazinoquinoxaline 3,  which on reaction with sodium alkoxides affords the respective ring opened products i.e. 2-acylhydrazino-3-alkoxyquinoxalines 4.

 

 

 

P K Dubey*, A Naidu, S Vijaya & B George Vineel

 

 

 

 

 

 

 

 

577

Oxidation of alcohols with 1-butyl-4-aza-1-azo­nia­­bicyclo[2.2.2]octane chlorochromate (BAAOCC) under non-aqueous conditions

 IPC: Int.Cl.7 C 07 C 39/00

 

 

Text Box: 3

 

 

 

Abdol R Hajipour*, Hamid R Bagheri & Arnold E Ruoho

 

 

 

 

 

 

 

581

Synthesis of furo[2,3-d]pyrimidines using
in­organic solid support

 

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

Furo[2,3-d]pyrimidine derivatives have been synthe­sized by the condensation of furan-2-amino-3-ethyl­carboxylates with monosubstituted thioureas using inorganic solid support.

 

Mazaahir Kidwai*, Akkal Deo Mishra & Shilpi Saxena

 

 

 

 

 

 

 

585

Synthesis, characterization and evaluation of antimicrobial activity of Mannich bases of some 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thia­zolidinones

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

A series of 5-(N,N-disubstituted aminomethyl)-2-[(4-carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones 4a-m have been synthesized.

 

 

Handan Altıntaş*, Öznur Ateş, Ayşe Kocab­alkanli, Seher Birteksöz & Gülten Ötük

 

 

 

 

 

 

591

New 1,3-dipolar cycloadducts of 3-azidoacetyl­coumarins with DMAD and their antimicrobial activity

 IPC: Int.Cl.7 C 07 D 311/00 // A 61 P 31/04, 31/10

3-Bromoacetylcoumarins 1 have been  treated with sodium azide in aqueous acetone to give 3-azidoacetylcoumarins 2 which on further  reaction with dimethylacetylenedicarboxylate in dry xylene yield 1,3-dipolar cycloadducts 4.

 

 

Raviraj A Kusanur & Manohar V Kulkarni*

 

 

 

 

 

 

 

 

595

QSAR analysis of a few GABA aminotransferase inhibitors as potent antiepileptics

 IPC: Int.Cl.7 C 07 C 229/00

QSAR analysis has been performed on a series of GABA-AT inhibitors in order to optimize physico­chemical and structural features for potent biological activity.

 

 

M S Vijay Kanth & S C Chaturvedi*

 

 

 

 

 

 

 

600

Importance of sulfoxidation in rapid race­misa­tion of glitazones

 IPC: Int.Cl.7 C 07 D 283/02

Semi-empirical AM1 studies have been carried out to propose the mechanism of rapid racemisation in glitazones taking place through the sulfoxidation of the thiazolidinedione ring.

 

 

Majid Ahmed, Smriti Khanna & Prasad V Bharatam*

 

 

 

 

 

 

 

607

Chemical investigation of the marine sponges Clathria reinwardti and Haliclona cribricutis

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

 

 

 

T Venkateshwar Goud, P Krishnaiah, S Malla Reddy, M Srinivasulu, M Rama Rao & Y Venkateswarlu*

 

 

 

Notes

 

 

 

611

Stereoselective synthesis of (2R, 3S, 22R, 23E)-
6, 6-ethylenedioxy-22-hydroxy-2, 3-isopropyl­idene­­dioxy-24-methyl-5
a-cholest-23-ene: An inter­me­di­ate for the synthesis of castasterone, dolicho­sterone and brassinolide

 IPC: Int.Cl.7 C 07 J 5/00, 9/00

A new efficient formal total synthesis of plant growth promoters such as castasterone, dolichosterone and brassinolide is described.

 

 

Braja G Hazra*, Tirunahari Pavan Kumar & Vandana S Pore

 

 

 

 

 

 

 

615

Synthesis of triphenylmethane derivative: Bisa­codyl

 IPC: Int.Cl.7 C 07 C 15/14

Lewis acid catalysed (AlCl3) rearrangement of phenyl picolinate 4 at 160°C to form 5a  and the reaction of 5a with phenol by using H3PO4 to form 1 is described.

 

 

Hari Babu Mereyala* & Kalyani Sambaru

 

 

 

 

 

 

 

618

Synthesis of 2,3-trans-3,4-trans-2-aryl-3-alkyl/aryl-chroman-4-ols

 IPC: Int.Cl.7 C 07 D 311/30

 

 

 

M Venkati & G L David Krupadanam

 

 

 

 

 

 

 

622

Synthesis of substituted and unsubstituted 2,4-diaryl-5-oxo-5,6,7,8-tetrahydro-2-chromens

 IPC: Int.Cl.7 C 07 D 311/00

 

 

 

M Giasuddin Ahmed*, Syeda Asghari Ahmed, U K R Romman, A Sultana Touchy, Mizanur Rahman Badal, Mohammad Awlad Hossain & Md Khabir Uddin

 

 

 

 

 

 

625

Novel synthesis and ring closure reactions of
3-hydrazino-1,2,4-triazolo[3,4-b]benzothiazole

 IPC: Int.Cl.7 C 07 D 277/62

3-Hydrazino-1,2,4-triazolo[3,4-b]benzothiazole on treatment with urea, carbon disulphide, sodium nitrite and aryl aldehydes affords corresponding cyclised products.

 

 

S B Kapratwar, K G Baheti & S V Kuberkar*

 

 

 

 

                                                                                                                                                                                                                                                                                                                                                         

 

 

 

628

Bridgehead nitrogen heterocyclic system: Facile synthesis and bioactivity of s-triazolo[3,4-b][1,3,4]thiadiazoles, s-triazolo[3,4-b] [1,3,4] thia­diazines and related heterocycles

 IPC: Int.Cl.7 C 07 D 285/12

The reaction of 3-p-hydroxypheny1-4-amino-5-mercapto-s-triazole 1 with various reagents to afford a variety of novel polycyclic heterocyclic systems is described.

 

 

 

Jag Mohan

 

 

 

 

 

 

 

631

Novel bridgehead nitrogen bisheterocyclic systems: Synthesis, stereochemistry and anti­microbial activity of p-bis[2H, 5H-4-oxo-thiazol-3-yl]phenylenes and p-bis[cis-5H-3,3a-dihydro­pyrazolo[3,4-d]thiazol-6-yl]phenylenes

 

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

The facile synthesis of p-bis[cis-3,3a-dihydro-5H-pyra­zolo[3,4-d]thiazol-6-yl]phenylenes 4 has been achieved by the condensation of p-bis[4-substituted phenylimine]phenylenes 1 with thioglycollic acid in toluene, using Dean-Stark water separator, to give p-bis[2H,5H-4-oxo-2-(p-substituted phenyl)­thiazol-3-yl]phenylene 2, which on condensation with aryl­aldehydes furnishes 5-arylidene derivatives 3 followed by treatment with 2,4-dinitro­p­henyl­hydrazine.

 

 

 

 

Jag Mohan* & Ashok Kumar

 

 

 

 

 

 

 

635

Ecofriendly solvent free microwave enhanced thermal Fries rearrangement of anilides and phenyl ureas

IPC: Int.Cl.7 C 07 C 211/46

A rapid and efficient microwave induced synthesis of aminoaryl ketones and aminoaryl amides is reported.

 

 

M Easwaramurthy, R Ravikumar, A J Lakshmanan & G J Raju*

 

 

 

 

 

 

 

638

Synthesis and antimicrobial activity of 1,3,5-thiadiazines and their isomerism into 1,3,5-triazines

 IPC: Int.Cl.7 C 07 D 285/34 // A61 P 31/04

A series of 2,6-diphenylimino-4-(substituted)- benzyl­­ideneamino-1,3,5-thiadiazines 4a-g have been synthe­sized and isomerized into corresponding 1-phenyl-2-phenylimino-4-(substituted) benzylidene-amino-6-thio-1,3,5-triazines 7a-g.

 

 

 

Pradip P Deohate* & B N Berad

 

 

 

 

 

 

 

643

Structural characterization of a glucan from the tubers of Curcuma aeruginosa

IPC:Int.Cl.7 A 61 K 35/00, C 07 H

The structure of glucan from the tubers of Curcuma aeruginosa has been determined by certain chemical methods and NMR spectral analysis.

 

 

C E Ranjini & K K Vijayan*

 

 

 

 

 

 

 

 

648

Two novel acyl sucroses from Petunia nyctaginiflora

 

IPC: Int.Cl.7 C 07 H // A 61 K 35/00

Two acyl sucroses, isolated from Petunia nyctaginiflora (Solanaceae) are  characterized as 2,3,4-(5-methylhexanoyl)-a-d-glucopyranosyl-b-d-6- acetylfructofuranoside 4 and 2,3,4-(6-methylhexano)-a-d- glucopyranosyl-b-d-6-acetylfructofuranoside 6.

 

4: R =-(CH2)3-CH(CH3)2; R1 = H; R2 =-COCH3

6: R =-(CH2)4-CH(CH3)2; R1 = H; R2 =-COCH3

 

A Sajeli Begum, Ajay Pratap Singh Mahendra Sahai*, Subhra Singh & Yoshinori Fujimoto

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.: International Classification 7  edition, 1999