Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

Total visitors: 2,197  since 16-06-06

VOL. 45B

NUMBER 6

JUNE 2006

CONTENTS

Papers

 

 

 

1426

Synthesis and NMR spectral studies of some new
1-heteroaryl-5-amino-3-alkyl/aryl-4-cyanopyrazoles

 

IPC: Int.Cl.8 C07D

 

 

 

 

 

 

 

 

Ranjana Aggarwal*, Vinod Kumar & Shiv P Singh

 

 

 

 

 

 

 

1431

Novel synthesis of heteroarylazopyrazolones and their application as disperse dyes via AlCl3-catalyzed diazocoupling of 1-aryl/heteroaryl-3-methyl-1H-pyrazol-2-in-5-ones in aqueous medium

 

IPC: Int.Cl.8 C07D

AlCl3-catalyzed diazocoupling of 1- aryl/heteroaryl-3-methyl-1H-pyrazol-2- in-5-ones 1 in water with different aryl/heteroaryldiazonium salts affords the corresponding azopyrazolones 2. Different fabrics have been dyed and their photostability and colour fastness identified.

 

 

 

 

 

 

 

Salem A Basaif, Mohamed A Hassan* & Adil A Gobouri

 

 

 

 

 

 

 

 

 

 

 

 

 

1437

Application of dipolar reagents towards complex heterocycles

 

IPC: Int.Cl8.  C07D

Novel complex heterocycles 2-13 have been obtained by the reaction of 1,2/1,3 and 1,4-benzenedicarboxaldehyde­hydra­zones and dicarboxaldoximes with 1,5-diaryl-1,4-pentadien-3-ones 1 in the presence of chloramine-T.

 

 

 

 

 

 

V Padmavathi*, K Venugopal Reddy,

B Jagan Mohan Reddy, A Padmaja & D Bhaskar Reddy

 

 

 

 

 

 

 

1443

Identification of pharmacophores for anti-inflammatory and analgesic activity on aryl-(imidazol-1-yl) acetates

 

IPC: Int.Cl.8 C07D

Pharmacophores for anti-inflammatory and analgesic activity have been identified based on aryl-(imidazol-1-yl) acetates in order to optimize physicochemical and structural features for potent biological activity.

 

 

 

 

 

 

R Sharma*, P S Shantanu Rao & S C Chaturvedi

 

 

 

 

 

 

 

1453

Synthesis and mass spectral fragmentation patterns of some thiazole and imidazolidine derivatives

 

IPC: Int.Cl.8 C07D

3-Substituted-4-oxoimidazolidine-2-thione 4 and 5-aryl-2-substituted thiazole 5 have been prepared via cyclization of compound 3 with ethyl chloroacetate and 4-substituted phenacyl bromide. The mass spectral fragmentation patterns of thiazole and imidazolidine are described.

 

 

 

 

 

 

 

S M Mohamed*, M Unis & H Abd El-Hady

 

 

 

 

 

 

 

 

 

 

 

 

 

1463

Synthesis of some novel 4-substituted coumarins having potential biological activity (Part III)

 

IPC: Int.Cl.8 C07D

The Schiff bases obtained by condensation of various substituted formyl coumarins with aromatic amines have been reacted with thioglycolic acid to give five membered cyclised product, 4-thiazolidinone substituted at 4-position of coumarins. 4-Alkyl coumarin-acetates have been successfully condensed with semicarbazide or thiosemicarbazide in polyphosphoric acid to yield amino substituted oxadiazoles and thiadiazoles. The intermediates and the title compounds have been characterized by their analysis and spectral data.

 

 

 

 

U C Mashelkar* & A A Audi

 

 

 

 

 

 

 

1470

Synthesis and behaviour of 2-carboxyvinyl-6,8-dibromo-4H-3,1-benzoxazin-4-one towards nitrogen, carbon and sulphur nucleophiles

 

IPC: Int.Cl.8 C07D

Interaction of 6,8-dibromoanthranilic acid with maleic anhydride in boiling n-butanol yields the malanilic acid derivative, which undergoes ring closure by heating with acetic anhydride and gives the 4H-3,1-benzoxazin-4-one derivative. Hetero-ring opening of the oxazinone nucleus by hydrazine hydrate in boiling ethanol followed by cyclisation affords the pyridazinoquinazolinone derivative. Benzoylation of the latter gives compound 21. 

 

 

 

 

M A El-Hashash*, T M Abdel-Rahman &

Y A El-Badry

 

 

 

 

 

 

 

 

 

 

 

 

 

1478

Cytotoxic and antimicrobial activities of some synthetic flavones

 

IPC: Int.Cl.8 C07D

A number of flavones have been synthesized and the biocidal activity of these flavones along with their corresponding chalcones have been investigated against some bacterial and fungal strains as well as brine shrimp nauplii. Some flavones showed good antibacterial, antifungal and cytotoxic activity against some selected bacterial and fungal strains as well as brine shrimp nauplii.

 

 

1  R1, R2 = -OCH3

4  R3, R4, R6 = -H, R5 = -CH3

11 R1, R2 = -OCH3, R3, R4, R6 = -H, R5 = -CH3

2  R1, R2 = -H

5  R4 = -H, R3, R5, R6 = -OCH3

12 R1, R2, R4 = -H, R3, R5, R6 = -OCH3

3  R1 = -H, R2 = -OH

6  R3, R6 = -H, R4 = -OH, R5 = -OCH3

13 R1, R3, R6 = -H, R2, R4 = -OH, R5 = -OCH3

 

 

14 R1, R2, R3, R4, R6 = -H, R5 = -CH3

 

 

 

 

 

 

 

Sohel Mostahar, Sayed Alam* & Azizul Islam

 

 

 

 

 

 

 

1487

Synthesis of 12,13-dihydro-5-oxoquinolino[2,3-a]carba­zoles, 3,11-dihydro-2,4-dioxopyrano[2,3-a]carbazoles and quinolino[2,3-b]carbazolo[6,5-a]pyran-7,8-diones

 

IPC: Int.Cl.8 C07D

 

 

 

 

 

 

 

 

 

V Sangeetha & K J Rajendra Prasad*

 

 

 

 

 

 

 

 

 

 

 

 

 

1492

Microwave assisted fast and clean conversion of mesylate to azide: Synthesis of (1S,2R/1R,2S)-1-azido-2-carbo­cyclic amines as immediate precursors to versatile 1,2-cis-diamines

 

IPC: Int.Cl.8 C07D

Efficient and rapid conversion of mesylate to azide under microwave irradiation has been demonstrated. It proceeds through inversion of configuration.

 

 

T Govindaraju

 

 

 

 

 

 

 

1499

Chemoselective synthesis of heterocyclic derivatives of 18-nor equilenine, 16-substituted-12H-11-oxa-15-aza-17-thia-cyclopenta[a]phenanthrenene and their in vitro evaluation of antibacterial and antifungal activity

 

IPC: Int.Cl.8 C07D

Chemoselective synthesis of heterocyclic derivatives of 18-norequilenine, 16-substituted-12H-11-oxa-15-aza-17-thiacyclo­penta[a]phenanthrene 4a-j is presented. These molecules 4a-j have exhibited moderate to good antibacterial activity against some gram-positive and gram-negative bacteria.

 

             2a,b                                      3a-e                                                 4a-j                                               5a-b

 

 

N J Malviya, A M Kulkarni, D Jaimini, B L Jadhav &

A V Karnik*

 

 

 

 

 

 

 

1504

One pot facile synthesis of 5-alkyl-1,2-dihydro-spiro[4H-3,1-benzoxazine-2,3¢[3H]indol]-4,2¢-diones under micro­wave irradiation

 

IPC: Int.Cl.8 C07D

A facile synthesis of some novel 5-alkyl-1,2-dihydro-spiro[4H-3,1-benzoxazine-2,3¢[3H]indol]-4,2¢-diones, in high yields, has been carried out classically as well as under microwave irradiation in solvent free conditions. Besides this, some novel 6-alkylanthranilic acids required for the synthesis of new spiro compounds have also been synthesized. The importance of alkyl substituent at C-6 position in anthranilic acid has been recognized again in such a cyclocondensation reaction, even when it is carried out under microwave irradiation. This is also supported by molecular modelling.

 

 

Anjali Saxena, Pankaj Khanna, Sunita Bhagat,

Archana Gupta & Subhash C Jain*

 

 

 

 

 

 

 

 

 

 

1511

New dammarane triterpenoidal saponins from Bacopa monniera

 

IPC: Int.Cl.8 C07C

Two new dammarane triterpenoidal saponins, designated as Bacoside A4 and A5, have been isolated from aqueous extract of Bacopa monniera Wettst. The structures have been elucidated as 3-O-a-l-arabinopyranosyl jujubogenin 1 and 20-O-a-l-arabinopyranosyl jujubogenin 2 on elaborate spectro­scopy and have been biologically tested in vitro in NBT reduction and chemiluminescence assays to draw useful structure activity relationship.

 

 

 

R S Pawar & K K Bhutani*

 

 

 

 

 

 

1515

Steroidal saponins from the roots of Asparagus adscendens Roxb and Asparagus racemosus Willd

 

IPC: Int.Cl.8 A61K

Two new sarsasapogenin glycosides 1 and 10, one each from Asparagus adscendens Roxb. and Asparagus racemosus Willd. have been isolated and structure elucidation accomplished using NMR studies. Two compounds 6 and 9 have been found in A. racemosus for the first time.

 

 

 

A N Jadhav & K K Bhutani*

 

 

 

 

 

 

 

1525

Synthesis of 1,5-benzothiazepines: Part XXXII- Synthesis and antimicrobial studies of 8-substituted-2,5-dihydro-2-(4-pyridyl)-4-(2-thienyl)-1,5-benzothiazepines

 

IPC: Int.Cl.8 C07D

 

 

Compd

5a

5b

5c

5d

5e

5f

X

F

Cl

Br

CH3

OCH3

OC2H5

 

Seema Pant, Hem Chandra, Priyanka Sharma &

Umesh C Pant*

 

 

 

 

 

 

 

 

 

 

 

 

 

1531

Stereochemistry of N5‑acyltetra­hydro‑1,5‑benzo­diaze­pines – NMR spectra and semiempirical MO calculations

 

IPC: Int.Cl.8 C07D

The three N5-acyltetrahydro-1,5-benzodiazepines prefer boat conformations BE on the basis of observations made from NMR spectra and semiempirical MO calculations

 

 

 

M Venkatraj, R Jeyaraman & S Ponnuswamy*

 

 

 

 

 

Notes

 

 

 

1541

Regeneration of carbonyl compounds from oximes, semicarbazones and tosylhydrazones with calcium hypochlorite and moist montmorillonite K-10

 

 

IPC: Int.Cl.8 C07C

Oximes, semicarbazones and tosylhydrazones, are converted into the corresponding carbonyl compounds in the presence of calcium hypochlorite and moist montmorillonite K-10 under mild and heterogeneous conditions.

 

 

 

 

Barahman Movassagh* & Ebrahim Dahaghin

 

 

 

 

 

 

 

1544

Two 2-naphthoic acids from Diospyros paniculata

 

IPC: Int.Cl.8 C07C

Phytochemical  investigation of the heartwood, root and stem of   Diospyros paniculata results in the isolation of 2-naphthoic acids 1 and 2, 2-naphthaldehydes, naphthoquinones, steroids and terpenoids.

 

1

2

 

S A Noor Mohamed, R Gandhidasan* & J A Charles

 

 

 

 

 

 

 

1547

Protection of aldehydes as 1,1-diacetates and deprotec­tion of 1,1-diacetates to aldehydes

 

IPC: Int.Cl.8 C07C

A safe and convenient method is reported for the  protection of aldehydes as 1,1-diacetates using Ac2O/acidic alumina and deprotection of 1,1-diacetates to  aldehydes using acidic alumina under MW irradiation.

 

 

 

 

 

 

Puja Nanda, Satya Paul & Rajive Gupta*

 

 

 

 

 

 

 

 

 

 

 

 

 

1551

Synthesis of new ellagic acid derivatives

 

IPC: Int.Cl.8 C07C

Ellagic acid has been isolated from Punica granatum. A series of hexahydroxydiphenyl derivatives of ellagic acid have been synthesized and characterized by spectroscopic analysis.

 

 

P D Jadhav & K S Laddha*

 

 

 

 

 

 

 

1554

Synthesis of homoanisic acid

 

IPC: Int.Cl.8 C07C

Synthesis of homoanisic acid by Erlenmeyer condensation via the formation of azalactone is discussed.

 

 

S S Mahajan* & R P Pikle

 

 

 

 

 

 

 

1557

Synthesis and pesticidal activities of some substituted pyridine derivatives

 

IPC: Int.Cl.8 C07D

Some pyridinylthiazolylazetidinones, pyridinylthiazolylthia­zolidi­nones and pyridinylthia-zolylformazans have been synthesized. Their structural assignments are based on structure and elemental analysis. These compounds have also been evaluated for insecticidal and antimicrobial activities.

 

 

Tripti Singh, Shalabh Sharma, VK Srivastava &

Ashok Kumar*

 

 

 

 

 

 

 

 

 

 

 

 

 

1564

A convenient synthesis of 2-chlorobenzo[b][1,8]naphthy­ridines

 

IPC: Int.Cl.8 C07D

2-Chlorobenzo[b][1,8]naphthyridines 4a-f have been synthesised in good yields utilizing 3-(2-chloro-3-quinolyl) acrylic acids 2a-f as the starting compounds.

 

 

J Christobel Vandana, L Ragunath & S P Rajendran*

 

 

 

 

 

 

 

1567

Steroid and aliphatic esters from the seeds of Nigella sativa

 

IPC: Int.Cl.8 C07C

Three novel compounds, one steroid and two esters have been isolated and identified as ergosta-5,24(28)-dien-2, 3-cis-diol 1, pentyl undecanoate 2, and methyloctadeca 14,16-dienoate 3.

 

 

 

 

B K Mehta*, Meenal Gupta & Manjul Verma

 

 

 

 

 

 

 

 

 

 

 

 

 

1572

Synthesis of 2-(aryl methylene)-(1H)- indane-1,3-(2H)-diones as potential fungicidal and bactericidal agents

 

IPC: Int.Cl8. C07C

Reaction between indane-1,3-dione 3 and different aromatic aldehydes 4 in the presence of piperidine and ethanol affords the compounds 5a-h. All the derivatives are evaluated for their antifungal and antibacterial activity against different strains.

 

 

 

3                   4                                                                         5a-h

 

S Meena*, D Shankar, K V Ramseshu, D Giles,

M S Prakash & S Venkataraman

 

 

 

 

 

 

 

1576

Facile preparation of amides from azo compounds by SmI2

 

IPC: Int.Cl.8 C07C

Azo compounds are conveniently reduced by SmI2/THF system and successively acylated smoothly with aromatic or aliphatic acyl chlorides or acid anhydrides to afford corresponding amides in one pot under mild and neutral conditions.

 

 

 

 

Xue Li & Yongmin Zhang*

 

 

 

 

 

 

 

1579

Reaction and antimicrobial activity of 1-aryle­thylene benzofuranyl ketone derivatives

 

IPC: Int.Cl.8 C07D

Interaction of benzalvisnaginone or khellinone derivatives with thiourea gives the tetrahydropyrimidin-2-thione derivatives which are condensed with dichloroacetic acid in acetic anhydride to form thiazolo[3,2-a]pytimidin-3-one. Reaction with quinidine, 2,3-dichloro-1,4-naphthoquinone and 2-aminothiazole chloroacetamide is investigated. The compounds are tested for antibacterial activity.

 

 

 

J A A Micky*, N M Saleh, S M Mohamed,

S A Mohamed & M M Salem

 

 

 

 

 

 

 

1584

Microwave induced eco-friendly solvent-free synthesis of 6-arylquinazolino[3,2-a] +[1,8]naphthyridin-13-ones

 

IPC: Int.Cl.8 C07D

An efficient and rapid synthesis of 6-aryl-quinazolino
[3,2-a][1,8]naphthyridin-13-ones 3 under microwave irradia­tion in a solvent-free condition is reported.

 

 

 

K Mogilaiah*, J Uma Rani & B Sakram

 

 

 

 

 

 

 

 

 

 

 

 

 

1587

Zinc-mediated allylation reactions of aldehydes and ketones in aqueous media under ultrasonic irradiation

 

IPC: Cl.8 C07C

The allylation reaction between aromatic aldehydes or ketones and allyl bromide are carried out in 83-100% yield with Zn-THF-NH4Cl under ultrasound irradiation at r.t. for 10 min.

 

 

 

 

Yan-Jiang Bian*, Chun-Ran Fan , Xiao-Hong Hu,

Ji-Tai Li

 

 

 

 

 

 

 

1591

Urea-hydrogen peroxide and microwave: An eco-friendly blend for allylic oxidation of alkenes with catalytic selenium dioxide

 

IPC: Int.Cl.8 C07C,C07D

Urea-hydrogen peroxide (UHP), in the presence of catalytic quantities of SeO2, under microwave irradiation led to the allylic oxidation of vinyl methyls while keeping the other chemical functionalities intact.

 

 

 

 

 

R Manktala*, R S Dhillon & B R Chhabra

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int.Cl8.: International Classification, 8th Edition, 2006