Indian Journal of Chemistry

VOL. 45B

NUMBER 4

APRIL 2006

933 Studies on spiroheterocycles part-I: Installation of biologically active heterocyclic nuclei into spiro compounds derived from cyclohexanone and diphenyl thiobarbituric acid

R K Behera*, A K Behera, Rosy Pradhan &
M Patra

The spiro compounds 2 have been synthesised. Heterocyclic units such as pyrazole, isoxazole and pyrimidine have been installed into the spiro compound through arylidene derivatives 3

943 Epoxidation and oxidation reactions using divinyl benzene crosslinked polystyrene supported t-butyl hydroperoxide

M S Sheela & K Sreekumar*

Divinyl benzene (DVB) crosslinked polystyrene supported t-butyl hydroperoxide resin has been prepared and employed in the epoxidation of olefins and oxidation of alcohols.

959 A facile synthesis of steroidal pyrazoles, isoxazoles and pyrimidines from testosterone

3.  X  =   NH, R =   H

4.  X  =   NH, R =   SCH₃

5.  X  =   O, R    =   H

6.             X             =              O, R                =              SCH₃

Ch Brajakishor Singh & L Warjeet Singh^*

Synthesis of 17b-hydroxy-androst-4-eno[3,2-c]pyrazole 3, 17b-hydroxy-androst-4-eno[3,2-c]-1¢H-5¢ -methylthio-pyrazole 4, 17b-hydroxy-androst-4-eno[2,3-d]isoxazole 5, 17b-hydroxy-androst-4-eno[2,3-d] -1¢H-3¢-methylthio isoxazole 6, 17b-hydroxy-androst-4-eno[3,2-d]-2¢-amino-6 ¢-ethoxypyrimidine 7, 17b,2¢-dihydroxy-androst-4-eno[3,2-d]- 6¢-ethoxypyrimidine 8, and 17b-hydroxy-androst-4-eno[3,2-d]-2¢-thiolo-6 ¢-ethoxypyrimidine 9, 17b-hydroxy-4-androsteno[3,2-d]-2¢-amino-6 ¢-ethoxypyrimidine 10, 17b,2¢-dihydroxy-4-androsteno[3,2-d]-6¢ ethoxypyrimidine 11, 17b-hydroxy-4-androsteno[3,2-d]-2¢-thiolo-6 ¢-ethoxypyrimidine 12, from 2-ethoxymethylene-4-androsten-3-one 1 and 2-bis (methylthio) methylene-4-androsten-3-one 2 are reported.

     7.   R   =   NH₂, R¢  =   H

     8.   R   =   OH, R¢   =   H

     9.   R   =   SH, R¢    =   H

   10.   R   =   NH₂, R¢  =   OEt

   11.   R   =   OH, R¢   =   OEt

                12.           R             =              SH, R¢     =              OEt

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

Coumarin 4-methyl acetates are oxidized to coumarin-4-methyl glyoxylate using SeO₂ with high selectivity. The product thus obtained is analogous to the phenyl glyoxylic acid mehyl ester i.e., coumarin-4-methyl glyoxylate and was further used for the various synthetic manipulations of different nitrogen containing heterocycles such as benzopyrazinone, pyrimidopyrazinones, pyrido (2,3-b) pyrazinones, oxazolidinones, tetrazinine derivatives, 1, 2, 4- triazinones substituted at 4- position of the coumarin.

U C Mashelkar * & A A Audi

972 Natural kaolinitic clay: A remarkable catalyst for the highly regioselective chlorination of arenes with Cl₂ or SO₂Cl₂

B Jayachandran, Prodeep Phukan,

976 A new euphane triterpene and a lipid diester from oleo-gum resin of Boswellia serrata

Tarun Singh & R S Bhakuni

Two new compounds, a euphane triterpenoid, 20,22-epoxyeupha-24-ene-3-one and a long chain compound, 5,6-epoxytridecanyl-1-[4¢(5¢), 9¢(10¢)-ditetradecen], 13-[12¢¢(13¢¢)-pentadecen]-dioate were isolated from the oleo gum resin of the plant Boswellia serrata. The structures have been established on their spectral data and chemical

980 Synthesis and biological evaluation of new pyrimidine derivatives

O A Fathalla*, H H Radwan, S M Awad & M S Mohammad

980 Synthesis and biological evaluation of new pyrimidine derivatives

O A Fathalla*, H H  Radwan, S M Awad & M S Mohamed

986 MALDI-TOF-MS and HPAE-PAD-chromatographic analysis of xyloglucan oligosaccharides generated from Brassica campestris meal

Partha Ghosh,  Pradyot Ghosal & Bimalendu Ray*

Characterisation of xyloglucan oligosaccharides 1 through 4 generated from Brassica campestris meal by enzyme hydrolysis, sugar compositional and linkage analysis, HPAE-PAD-chromatography and MALADI-TOF-mass spectrometry has been carried out.

993 Synthesis of substituted 3-cyano-2-pyridones: Part IV. Influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalysed synthesis of substituted 3-cyano-2-pyridones

Dušan ÆZ Mijin*, Branislav D Mili«c &

Milica M Miši«c-Vukovi«c

Lipase from Candida rugosa has been used to study the influence of 3-alkyl-2,4-pentanedione and N-alkyl cyanoacetamide structure on the enzyme catalyzed reaction of pyridone ring formation in water at 40^oC.

1004 New anti-inflammatory active flavanone glycoside from the Echinops echinatus Roxb

R N Yadava* & S K Singh

A new anti-inflammatory active flavanone glycoside 5,7-dihydroxy-8,4¢-dimethoxyflavanone-5-O-a-l-rhamno -pyranosyl-7-O-b-d-arabinopyranosyl-(1®4 )-O-b-d-glucopyranoside A along with a known compound dihydroquercetin-4'-methyl ether B have been isolated from the leaves of Echinops echinatus.

1009 Condensed bridgehead nitrogen heterocyclic systems: Microwave assisted synthesis and bioactivity of s-triazolo[3,4-b][1,3,4]thiadiazoles, s-triazolo [3,4-b][1,3,4]thiadiazines and s-triazolo[3’,4’:2,3]-thiadiazino[5,6-b] quinoxaline

Mahendra Shiradkar* & Rajesh Kale

A rapid synthesis of title compounds under solvent free conditions using MWI is described.

Glyceride derivat

1014 Synthesis, biological evaluation and kinetic stud-ies of glyceride prodrugs of biphenyl acetic acid

M S Y Khan, Mymoona Akhter* & A Husain

Glyceride derivatives of biphenyl acetic acid have beensynthesized by reacting 1,2,3- trihydroxypropane-1,3-dipalmitate/stearate with the acid chloride of biphenyl ace-tic acid to reduce the gastrointestinal toxicity associatedwith it and are tested for their ulcerogenicity, anti-inflam-matory and analgesic activity and hydrolytic behaviour.

1020 Synthesis and surface active properties of con-densed and non condensed quinazoline deriva-tives of industrial application

M S Amine, A A Aly* & R El-Sayed

3,1-Benzoxazinone derivative 3 is used as a precursor forthe synthesis of novel quinazolines and annulatedquinazoline derivatives through reaction with different ni-trogen nucleophiles at different reaction conditions.

1028Synthesis of  pyrimido annelated carbazoles and4′-methyl-6-oxo-bisindolo [1,2- b:5,4-b′′′′′] cyclo-hexanones using 2-hydroxymethylene-1-oxo-1,2,3,4 tetrahydrocarbazoles

V Sangeetha & K J Rajendra Prasad*

Treatment  of  2-hydroxymethylene-1-oxo-1,2,3,4-tetrahydrocarbazoles 1a-d with guanidine nitrate affords 2-amino-4-hydroxy-1,4,5,6-tetrahydropyrimido[4,5-a]carbazoles 2a-d. In an another reaction, 2-hydroxymethylene-1-oxo-1,2,3,4-tetrahydrocarbazoles1a-d are treated with diazotized p-toluidine under Japp-Klingemann conditions to furnish the respective 4'-methyl-1-oxo-2-phenylhydrazono-1,2,3,4-tetrahydrocarbazoles3a-d, which upon cyclisation using Kent’s reagent(CH3COOH : HCl, 4:1) yield the corresponding 6,12-dihydro-2-methyl-6-oxo-bisindolo[1,2-b:5,4-b’]cyclohexanones 5a-d.

1034 Studies on organo phosphorous compounds:Reactions of benzosubarones and benzazepineswith Lawesson’s reagent

Venkateswarlu Peesapati* & Gannoji  Rupavani

The selective reduction of carbonyl group of various aro-matic and aliphatic compounds bearing different functionalgroups with sodium borohydride in the presence of clay inaprotic solvents give 72-93% yield of correspondingalcohols.

1041 Design and synthesis of new spiroheterocycles:Selective role of potassium fluoride in DMF

Madhukar S Chande* & Udayashankar S Bhat

Potassium fluoride (KF) in dimethyl formamide (DMF) isfound to be very effective and selective in the synthesisof spiro compounds. 4-Bromo-4-carbethoxy-(4H)-1-phenyl-3-substituted-pyrazol-5-ones are selectivelyconverted to spiro derivatives.

1048Solvent free N-alkylation of phenyl sulfanilidesunder microwave irradiation

P Jaisankar  &  P C Srinivasan*

An efficient and fast synthesis of 1,8-naphthyridines 3 from2-aminonicotinaldehyde 1 and carbonyl compounds contain-ing α-methylene group 2 using ammonium acetate in sol-vent-free condition under microwave irradiation has beenreported.

1054 An efficient procedure for the synthesis of 1,1-diacetates from aldehydes with acetic anhydridecatalyzed by silica sulfate

Tong-Shou Jin*, Ying Zhao, Shu-Qing Gu,Li-Bin Liu & Tong-Shuang Li

The reaction of aldehyde with acetic anhydride catalyzed bysilica sulfate results in 1,1-diacetates in high yields at roomtemperature.

1057Rapid and efficient microwave-assisted  synthe-sis of 4-amino-3-mercapto-5-substituted-1,2,4-triazoles

S S Joshi & A V Karnik*

4-Amino-3-mercapto-5-substituted-1,2,4-triazoles 3a-g havebeen synthesized in a few minutes (8-10 min) under micro-wave irradiation in 66-74% yield.

1060 Change of triterpene profile in the extracts ofDysoxylum species on prolonged preservation

M D Ajitha bai, G Jayakumar*,Pillai Saritha Balakrishna & R Salini

Triterpene profile is found to change when the extract andleaf samples kept for a period of four to five years are re-examined. The variety disappears and the distribution isfound to converge to one structure. The total yield percent-age is however unaffected. Results with two of Dysoxylumspecies are presented.

1063Synthesis and biological activities of prenylatedtyrosine derivatives, the metabolites ofPithomyces ellis

Somepalli Venkateswarlu, Gopala KPanchagnula & Gottumukkala V Subbaraju*

2-[4-((2E)-3-Methylbut-2-enyloxy)phenyl]- ethan-1-ol 3 and3-[4-(2E)-3-methylbut-2-enyloxy)phenyl]-2-(acetylamino)propanoic acid 8 have been synthesized from4-hydroxyphenylacetic acid, L-tyrosine respectively. Theyshow significant brine shrimp lethality, weak antioxidant andantibacterial activities.

1067Synthesis of some substituted 2-oxo-1,2,3,4tetrahydropyrimidines (3,4-dihydropyrimidin-2(1H)-ones) and 2-thioxo-1,2,3,4-tetrahydropy-rimidines catalyzed by tin(II) chloride dihydrateand tin (II) iodide under microwave irradiation

Dipak K Roy & Manobjyoti Bordoloi*

A simple, economic and efficient one pot synthesis of somesubstituted 2-oxo-1,2,3,4-tetrahydropyrimidines (3,4-dihydropyri-midin-2(1H)-ones) and 2-thioxo-1,2,3,4-tetrahydropyrimidines under solvent free condition and mi-crowave irradiation catalyzed by tin(II) chloride dihydrateand tin (II) iodide is described.

1072Synthesis and antibacterial activity ofthiosemicarbazones

A K Parekh* & K K Desai

4-Aryl-3-thiosemicarbazones 3a-h have been prepared bythe reaction of 4-aryl-3-thiosemicarbazides 1a-h with 2-hy-droxy-4-isopropoxy-5-nitroacetophenone in presence of fewdrops of acetic acid in aqueous ethanol.

1076A facile one-pot synthetic route to substitutedfused tetrahydropyrimidines. Part 41: Synthesisof 1-(aralkyl/aryl)-3-(alkyl/aralkyl/aryl)-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazolines and 1-(aralkyl/aryl)-3-(alkyl/aralkyl/aryl)-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazolines

Kaushik Chanda, Milan C Dutta &Jai N Vishwakarma*

A facile one pot pathway has been developed for the syn-thesis of novel 1-(aralkyl/aryl)-3-(alkyl/aralkyl/aryl)-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazolines 2a-e and 1-(aralkyl/aryl)-3-(alkyl/aralkyl/aryl)-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazolines 2f-k by thecyclocondensation of cyclic enaminones 1a-d with formal-dehyde and primary amines in refluxing methanol in goodyields.

1080An efficient and time saving microwave-assistedselenium dioxide oxidation of 1,2 diarylethanones

S T Shirude, P Patel, R Giridhar &  M R Yadav*

Selenium dioxide oxidation of 1,2-diarylethanones to cor-responding diones under microwave radiations using dim-ethylsulfoxide as solvent, as an efficient and  time savingmethod is reported.

1086 An efficient and product selective reduction ofazoxyarenes into azoarenes or hydrazoarenes bytin/hydrazine hydrate

H M Nanjundaswamy & M A Pasha*

Azoxyarenes on treatment with hydrazine hydrate/tin inmethanol gives the corresponding hydrazoarenes andazoarenes under microwave irradiation and at reflux condi-tions, respectively.  The reaction is very fast, and gives ex-cellent yield of the product. Substituents like CH3, OCH3,OC2H5 and Cl are unaffected.

Letter to the Editor

1090

Evaluation of 13C NMR data for C-methylatedflavonoids: A literature investigationPawan K Agrawal

1092

  Additions and Corrections

Authors for correspondence are indicated by (*)

IPC:International Patent ClassificationInt. Cl7

.International Patent Classification, 7th Edition, 1999