Total visitors: 3,724  since 19-11-04

Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

VOLUME 43 B

NUMBER 11

NOVEMBER  2004

 

 

CONTENTS

 

Rapid Communications

 

2381

 

 

 

 

 

 

 

 

 

 

 

 

One pot synthesis of novel 1,2-dihydro-5-methyl-spiro[4H-3,1-benzoxazine-2,3¢[3H]indol]-4,2¢-diones

 

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

 

 

 

 

 

 

 

 

 

 

A facile one pot synthesis of some novel spiro heterocycles such as 5-methyl-spiro[benzoxazine-indol]-4,2¢-diones 3a-j is carried out by cyclo­condensation of indole-2,3-diones 1a-j with 6-methyl­anthranilic acid 2 in ethanol under dry condition. The importance of substituent at C-6 position in 2 has been highlighted in such condensation reactions. The molecular modelling has shown that such substitution perfectly aligns the carboxyl group for intramolecular cyclization to take place. The reaction is of great value because of its environmentally benign character as non-toxic chemicals are used and no waste is generated.

 

 

Anjali Saxena, Rajeev Goswami, Pankaj Khanna, Sunita Bhagat & Subhash C Jain*

 

Papers

 

2386

 

 

 

 

 

 

 

Synthesis of some blocked di- and trisaccharide derivatives related to the repeating unit of the O-antigen from Shigella dysenteriae type 3 in the form of their glycosides

 

IPC: Int.Cl.7 C 07 H 3/04, 3/06

 

 

 

 

 

 

 

 

 

 

  Sujit Kumar Sarkar & Nirmolendu Roy*  

2395

 

 

 

 

 

Synthesis of mono and bis pyrazolines and iso­xazolines by 1,3-dipolar cycloaddition of dipolar reagents to 3,3'-[1,4-/1,3-phenylene]bis [1-aryl-2-propenone] in the presence of chloramine-T

 

IPC: Int.Cl.7 C 07 C 45/00

 

Mono, bis pyrazolines and isoxazolines have been prepared by the 1,3-dipolar cycloaddition of nitrile imines and nitrile oxides to 3,3'-[1,4-/1,3-phenylene]bis[1-aryl-2-propenone] in the presence of chloramine-T.


 

 

 

 

V Padmavathi*, G Sivajyothi, N Y Sreedhar, K Venugopal Reddy & A Padmaja

 

2401

 

 

 

 

Benzopyrans: Part 46 ¾ Reactions of 3-ben­zoyl-2-bromomethyl-1-benzopyran-4-one with some bisnucleophiles

 

IPC: Int.Cl.7 C 07 D 311/04

 

Bromine in the title bromomethylpyranone 2 can be substituted by sodium acetate, phenylhydrazine and thiourea. The substrate 2 gives the pyrano fused heterocycles 9-11 with NH2YH (Y = O, NH, NPh) and 16 with thioacetamide.

 

 

Chandra Kanta Ghosh*, Sumit Kumar Karak & Ajit Kumar Chakravarty

 

2405

 

 

 

 

Synthesis and utility of 2-acetyl-1-hydroxy­carba­zoles — Synthesis of 2-methyl-4-oxopyrano[2,3-a]carbazoles (indolochromones)

 

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

 

 

 

Vandana T, K J Rajendra Prasad* &D Sowmithran

 

2410

 

 

 

 

 

 

 

Synthesis and antimicrobial activity of 2-(4-formyl-3-pyrazolyl)-3-phenylindoles

 

IPC: Int.Cl.7 C 07 D 209/04 // A 61 P 31/04, 31/10

 

 

 

 

2-(4-Formyl-3-pyrazolyl)-3-phenylindoles 4 have been prepared by the action of Vilsmeier-Haack reagent (POCl3-DMF) on hydrazones derived from 2-acetyl-3-phenylindoles 2. The pyrazole derivatives 4 and their azines 5 are tested for their antimicrobial and antifungal activities. Fischer indolisation of a-phenylbutane-b,g-dione-b-3,4-dimethylphenyl hydra­zone 1d is also described.

 

 

Shambabu Joseph Maddirala, Vidya S Gokak & Linganagouda D Basanagoudar*

 

2416

 

 

 

 

 

 

 

 

 

Dual fluorescence and biological evaluation of paracetamol ethers from 4-bromomethyl­coumarins

 

IPC: Int.Cl.7 A 61 K 31/167

 

 

 

 

 

 

Paracetamol 1 has been reacted with 4-bromo­methylcoumarins 2 to obtain the corresponding ethers 3 which have been hydrolysed to the amino ethers 4. Structure of 4 has been confirmed by the chemo­selective reaction of 2 with p-aminophenol, which has also been found to yield the thermodynamically controlled products 5 at elevated temperatures. Compounds 3 have been found to exhibit dual fluorescence.

 

 

 

Lokesh A Shastri, Manjunath Ghate D & Manohar V Kulkarni*

 

2423

A facile synthesis of 2-aminobenzene-1,3-dicarbo­nitrile

 

IPC: Int.Cl.7 C 07 C 209/10

An efficient facile synthesis of 2-aminobenzene-1,3-dicarbonitrile using inorganic solid support under microwave activation is described and reaction time has been brought down from hours to minutes with improved yield as compared to conventional heating.

 

 

Mazaahir Kidwai*, Shilpi Saxena &  Shweta Rastogi

 

2426

 

 

 

 

Microwave assisted synthesis of phenyl(2-phenyl-5,6,7,8-tetrahydro-4-quinolinyl)methanone and its derivatives

 

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

 

 

 

H Surya Prakash Rao* & S P Senthilkumar

2431

Synthesis and comprehensive electrochemical investigations of 1-dichlorophosphino-2-phospha-3-phenyl-4-mercapto-5-aza-6-hydroxy-7-arylazo­indolizines

 

IPC: Int.Cl.7 C 25 B 3/00

The electrochemical reduction of 1-dichloro- phos­phino-2-phospha-3-phenyl-4 mercapt o-5-aza-6-hy­dro­xy-7-arylazoindolizines have been studied over wide pH range.The kinetic parameters have also been calculated.The synthesized compounds have been characterized by IR, NMR and elemental analyses.

 

                           R = (a) H, (b) 4'-OCH3, (c) 3'-Cl, (d) 2'-CH3, (e) 4'-COOH, (f) 4'-Cl
       
                           (g) 3'-OCH3, (h) 4'-Br, (i) 4'-COOCH3, (j) 3'-OH, (k) 4'-OH,
       
                          (l) 3'-CH
3

 

Pratibha Sharma*, Ashok Kumar & Shikha Sharma

 

2440

QSAR study of a series of 2,3,6 - substituted quinazolinones as AT1 selective angiotensin II receptor antagonists

 

IPC: Int.Cl.7 C 07 D 239/72

QSAR analysis on a series of twenty three quinazolinone derivatives has been performed to identify the essential physico-chemical features required for their AT1 antagonistic activity.

 

Trupti Pandya & S C Chaturvedi*

2446

 

 

A convenient approach towards separation and identification of triterpenes of Δ12 lupane series

 

IPC: Int.Cl.7 C 07 J 17/00

A convenient method is described towards separation and identification of  triterpenes of Δ12 lupane series.

 

                                                     1                                                                        2

 

 

Ram Sagar, Namrata Dilip Dhoke & Arun K Shaw*

 

2452

Constituents of high altitude Himalayan herb Angelica glauca*

 

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

(Z)-Ligustilide, (Z)-butylidinephthalide, methyl octadecadinoate, caryophyllene and caryophyllene oxide and have been isolated from the n-hexane extracts of root of Angelica glauca, collected from the high altitude region of Kumaun Himalayas in Uttaranchal.

 

 

(Z)-Ligustilide
 

(Z)-Butylidine phthalide
 

 

CH3-(CH2)9-CH2-CH=CH-(CH2)2-CH=CH-COOCH3

Methyloctadecadinoate

 

Caryophyllene oxide
 

 

 

Caryophyllene
 

 

K S Khetwal*, S K Pathak, K Sajwan,

Bharat Pandey & Alexey V Tkachev

 

Notes

 

2456

Sulfonyl acetic acids ¾ Source for substituted 2-oxazolines

 

IPC: Int.Cl.7 C 07 D 263/00

A new class of 2-oxazolines have been prepared from N-(2-chloroethyl)sulfonamides by base promoted cyclization with NaH in THF. All the compounds are characterized by IR and 1H NMR spectra. 

 

 

V Padmavathi*, B Chandra Obula Reddy, D R C Venkata Subbaiah & A Padmaj

2459

Synthesis of novel substituted tetrahydro­pyri­dines, pyrans and thiopyrans

 

IPC: Int.Cl.7 C 07 D 211/00, 309/00, 335/00

4,4-Disubstituted 2,6-diaryl-3,5-diaroyl-tetrahydro­pyridines/pyrans/thiopyrans are synthesized from 1,5-diaryl-3,3-dimethoxycarbonyl-1,5-pentanedione 1 /1, 5-diaryl-3-cyano-3-ethoxycarbonyl-1,5-pentanedione 2 /1,5-diaryl-3,3-dicyano-1,5-pentanedione 3. All the compounds have been characterized by spectral parameters.

 

 

V Padmavathi*, B Jagan Mohan Reddy, M Rajagopala Sarma & A Padmaja

 

     

2464

Sn/NH4Br assisted selective reduction of nitro­arenes into anilines under neutral conditions

 

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

A simple, cost-effective method for the reduction of aryl nitro compounds by tin in the presence of ammonium bromide in methanol to give anilines is reported.

 

M A Pasha* & V P Jayashankara

2467

 

 

 

 

 

 

 

A facile synthesis of 3,4-disubstituted-1,2-dihydro-5H-pyrrol-2-ones

 

IPC: Int.Cl.7 C 07 D 207/38

 

A facile and efficient method for the synthesis of 3,4-disubstituted-1,2-dihydro-5H-pyrrol-2-ones 8a,c-f is reported. The method involves the hydrogenation of cyanohydrins of 2-alkyl-3-oxobutyric acid alkyl esters 1a-f over Raney Ni at 50 psi to furnish hitherto unknown aminoacetyl intermediates 6a-f in quantitative yields, which are cyclised to the targeted compounds.

 

Kalpana Bhandari* & V L Sharma

2471

 

 

 

 

 

 

 

 

 

A facile route to enaminones: Synthesis of 3-alkyl/aralkyl/arylamino-1-arylprop-2-en-1-ones

 

IPC: Int.Cl.7 C 07 C 11/06, C07 D

 

Reactions of 3-dimethylamino-1-arylprop-2-en-1-ones 2 with arylamines in acetic acid at room temperature and with alkylamines or aralkylamines in refluxing ethanol give 3-arylamino-1-arylprop-2-en-1-ones 3a-j and 3-alkyl/aralkylamino-1-arylprop-2-en-1-ones 4a-f respectively in good to excellent yields. Enaminones 4a-f have also been synthesized, alternatively, by reacting 2 with appropriate amines under microwave irradiation in minutes giving much higher yields.

 

 

 

Milan Chandra Dutta, Kaushik Chanda, E Karim & J N Vishwakarma*

 

2475

 

 

 

An efficient microwave assisted solvent-free general route to cyclic enaminones

 

IPC: Int.Cl.7 C 07 C 49/543

 

1,3-Cyclohexanedione and dimedone have been reacted with primary amines in domestic microwave oven to give cyclic enaminones 2a-h in very good to excellent yields.

 

 

 

Kaushik Chanda, Milan Chandra Dutta &  J N Vishwakarma

 

2478

 

 

 

 

Neutral alumina- K2CO3: An eco-friendly system for synthesis of diaryl ethers under microwave irradiation

 

IPC: Int.Cl.7 C 07 C 41/00

 

 

A Venkat Narsaiah & K  Nagaiah*

2482

 

 

 

 

 

 

Nickel mediated Biginelli like three component coupling reaction : A solvent free microwave assisted synthesis of spiro-fused heterocycles

 

IPC: Int.Cl.7 C 07 D

 

Nickel mediated preparation of spiro-fused  heterocycles in solid state in a three component  coupling reaction using urea, aldehyde and  barbituric acid or meldrum's acid is reported which  is also accelerated by microwave irradiation and  cobalt chloride hexahydrate is found to be equally  effective.

 

 

Anil Saini, Sanjay Kumar & Jagir S Sandhu*

2485

Microwave assisted synthesis of thiadiazolo-pyrimidin-2-thiones

 

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

A series of 1-(1,3,4-thiadiazolo)-2-thioxo-pyrimidines are synthesized by the condensation of mono­substi­tuted thiourea ethyl acetoacetate and aryl aldehyde in dry media using microwave irradiation.  The reaction time is brought down from hours to minutes along with yield enhancement.

 

 

Mazaahir Kidwai*, Shashi Bala & Akkal Deo Mishra

 

2488

Microwave-induced acetoacetylation of isoxa ­zolyl amines with b-keto esters

 

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

The reaction of isoxazolyl amines with different b-keto esters under microwave irradiation, without using any catalyst and / or solvent leads to the formation of isoxazolyl amide derivatives by acetoacetylation.

 

E Rajanarendar*, K Ramu & D Karunakar

Authors for correspondence are indicated by (*)

                      

                                                         IPC: International Patent Classification

                                                         Int. Cl.: International Classification 7 edition, 1999