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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry










Rapid Communications















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*












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*  







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







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







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










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*












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*



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







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


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


Pratibha Sharma*, Ashok Kumar & Shikha Sharma



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*




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*



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)-Butylidine phthalide





Caryophyllene oxide





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

Bharat Pandey & Alexey V Tkachev





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


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




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









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











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*






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







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*








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*


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



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