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Indian Journal of Chemistry Sect. B: Organic Chemistry including Medicinal Chemistry


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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 40B

NUMBER 8

AUGUST 2001

CONTENTS

Papers




656

An efficient synthesis of trans--oxo-,-unsaturated carboxylic acids, the inter-mediates for patulolide A and pyrenophorin

K Joju Davis, U T Bhalerao & B Vittal Rao*

A convenient synthesis of 11-benzyloxy-4-oxo-(2E)-dodecenoic acid and 7-benzyloxy-4-oxo-(2E)-octenoic acid as the intermediates for the antifungal natural products patulolide A and pyrenophorin starting from 1,7-heptane diol and 1,3-propane diol respectively, are described.





















6

62


Effect of substituent on photoinduced ring opening of -epoxyketones by 2,4,6-triphe-nylpyrilium tetrafluoroborate (TPT)

H R Memarian*, A Hesami, F Nikpour &

D Döpp

Photocatalytic ring opening of some -epoxyketones has been investigated.



















667

Double Michael addition reactions of some new 1,5-diaryl-2-alkyl-1,4-peutadien-3-ones: Part II


V Padmavathi*, T V Ramanna Reddy,

K Venugopal Reddy, K Audisesha Reddy &

D Bhaskar Reddy

The reactivity of unsymmetrical 1,5-diaryl-2-alkyl-1,4-pentadien-3-ones with active methylene compounds has been studied.





















6

74


A convenient synthesis of antiviral acyclic
C-nucleosides incorporating 1,3,4-thiadiazine nucleus as a nucleobase


L D S Yadav*, Smita Singh & Suman Dubey

Antiviral acyclic C-nucleosides 6a-d and 7-d have been synthesised from the same precursors 4a-d by the action of 90% H2SO4 and gl AcOH, respectively.





















6

78


Synthesis and reactions of some new substituted phenylhydrazono indeno-thiazolo[3,2-b]-pyrimidine-3-ones of possible antimicrobial activity

M A Salama* & S A El-Essa






















682

Synthesis and bioefficacy evaluation of 2- [4-(3- arylprop -2- enoylphenoxy]- N-substituted acetamides and 2-[4-(5-aryl-4,3-dihydro-1H-pyrazol-3-yl)phenoxy]acetic acid hydrazides as potential pesticides

The title compounds, 2-[4-(3-arylprop-2-enoyl)phenoxy]-N-substituted acetamides (23-36) and 2-[4-(5-aryl-4,5-dihydro-1H-pyrazol-3-yl)phenoxy]-acetic acid hydra-zides (37-43) have been synthesized and evaluated for their toxicity against five phytopathogenic fungi, two saprophytic fungi, and one phytopathogenic bacterium. Some of the compounds inhibit the growth of S. sclerotiorum, A niger and X. campestris pv. Citrii at a concentration of 200 ppm.












Heetika Malik, Anjula Dahiya,
Rakesh Kumar, M S Sangwan,
Naresh Mehta & Naresh K Sangwan*























688

QSAR of matrix metalloproteinase inhibitor (S)-3-methyl-2-(substituted biphenyl-4-sulfonylamino)butyric acids using principal component factor analysis

Kunal Roy

QSAR and QAAR of biphenylsulfonamide matrix biphenylsulfonamide matrix matalloproteinase inhibitors have been performed using principal component factor analysis as the preprocessing step.





















698

Phytochemical investigation of aerial parts of Pluchea lanceolata C.B. Clarke

Mohd Ali*, Nasir Ali Siddiqui &

Ramidi Ramachandram

Six new phytoconstituents isolated from the aerial parts of Pluchea lanceolata have been formulated as 14,15-seco-urs-18-H-20(30)-en-3-yl acetate 1; 4,8-dimethyldo-deca-7Z-en-yl-9,10-dihydroxyundeca-1-oate 2; -do-triaconta-29,32-olide 3; 4-(2-ketobutylcylohexyl)-20-eincosan-14-ol-1-oic acid 4; 5,9,13,17-tetramethyl-18-en-8-ol-nona-decanoic acid octanyl ester 5; and 3,7,11-trimethyl dodeca-10-en-yl-n-hexadecan-9-ol-1­oate 6.









Notes


7

07


Synthesis of spiropyrazolines [5,9]anthrone

M Shanmugasundram, S Manikandan,

R Kumareshwaran & R Raghunathan*

Synthesis of series of novel spiropyrazoline[5,9]anthrone by the regioselective 1,3-dipolar cycloaddition of diphenylnitrilimine with 9-methyleneanthrone and 9-arylideneanthrone is described.




















710

Synthesis of substituted cyclohex-2-enones

M G Ahmed *, S A Ahmed, U K R Romman, K Akhter, M A Chowdhury & F Kiuchi





















7

13


Synthesis of 1,8-naphthyridines under solvent free conditions

K Mogilaiah* & R Babu Rao

An efficient and convenient synthesis of 1,8-naphthyridines 3 by the reaction of 2-aminonicotinaldehyde 1 with active methylene compounds 2 in the presence of piperidine under solvent free conditions is described.



















715

A simple and facile microwave assisted synthesis of 9-oxo-2(E)decenoic acid

Goverdhan L Kad*, Jasamrit Kaur,

Sandeep Nayyar, Irvinder Kaur &

Jasvinder Singh

Microwave assisted synthesis of 9-oxo-2(E)-decenoic acid, the queen bee substance, pheromone of Apis Melifera, has been accomplished utilizing alkylation/ decarboxylation and Knoevenagel condensation reactions.





















7

17


Microwave assisted synthesis of novel pyrazoles

Mazaahir Kidwai*, Rupak Kumar Aryal &

Preeti Misra

1,3,4-Trisubstituted pyrazoles have been synthesized by reaction of 2-methyl-2-phenyl propanoylhydrazide with substituted actophenone followed by Vilsmeier Haack reagent under microwave irradiation.



















719

Ferric chloride induced catalytic cleavage of oximes and hydrazones under solvent free conditions

D Subhas Bose*, A Venkat Narsaiah &

P Ravinder Goud





















722

Phenyl chloroformate: A convenient reagent for the preparation of nitriles from primary amides
D Subhas Bose*, S V Varadarajan &

G Vanajatha

A simple and efficient method for the synthesis of nitriles from primary amides in high yields using phenyl chloroformate and pyridine in CH2Cl2 at r.t. is described.





















724

Cetyltrimethylammonium cerium nitrate: A phase transferring oxidant


B K Mishra*, M Kuanar, A Sharma &

B B Nayak


A phase transferring oxidant has been synthesised, characterised and used for the oxidation of benzyl alcohol, hydroquinone, 8-hydroxyquinoline, 2-aminophenol, 1-naphthol and 2-naphthol.
[C16H33N+(CH3)3]2Ce(NO3)6



















7

27


Potassium peroxodisulfate: A convenient oxidizing agent for aromatization of 1,4-dihydropyridines

H R Memarian*, I Mohammadpoor-Baltork,

M M Sadeghi & Z S Samani

Potassium peroxidisulfate serves as an inexpensive reagent for efficient oxidation of 1,4-dihydropyridines to their corresponding pyridines.




















729

Synthesis and physico-chemical properties of aromatic polyesters containing S-triazines rings in the main chain

J B Shah, P M Patel, S K Patel & K C Patel*

Nine polyesters have been synthesized by high temperature polycondensation of 2-(-naphthylamino)-4,6-bis(naphtha-oxy-3-carbonyl chloride)-S-triazine (NANCCT) with each of the aromatic diols: bisphenol-A, bisphenol-C, 1,5- and 1,7-dihydroxynaphthalene, 1,4-di-hydroxyanthraquinone, phenolphthalein, catechol, resorcinol and hydroquinone (Hq). All polyesters have been characterized by physical, spectral and thermal studies.





















7

35


A comparison of the DNMR behaviour of methyl 5,6-bis-(2-methoxyphenyl)-1,4-di-methyl-7-oxo-bicyclo[2,2,1]hept-5-en-2-endo-carboxylate and its 7-oxa analogue


A Sampath Kumar, S Prahlada Rao &

S N Balasubrahmanyam*

Conformational transmission in the bicyclic system A is of such a nature that when the C(7) carbonyl is replaced by an ether kinkage (AB by ab inito synthesis) the VT-DNMR behaviour observed in the 1H NMR spectrum of A, most likely associated with hindered rotation of the o-methoxylphenyl groups, is not observable in B.




















742

Novel triheterocyclic systems by Mannich reaction on 3-arylsydnones: Synthesis of 3-aryl-4[2-(8-hydroxy-7-quinolinylimethyl-amino)thiazol-4-yl)] sydnones and 3-aryl-4[2-(3-acetyl-2-hydroxybenzylamino)-thi-azol-4-yl)sydnones as possible antimicrobial agents.

3-Aryl-4-(2-aminothiazol-4-yl)sydnones 2a-m when subjected to Mannich reaction with 8-hydroxyquinoline give the triheterocyclic Mannich bases 3b-m. Similar reaction with orthohydroxy acetophenone resulted in the formation of the methylamino derivatives 4a-m. All these compounds have been evaluated for antimicrobial activity, while compounds 3b-m have been screened for their antitubercular activity also.










Shanta G Mallur & Bharati V Badami*














7

48


Dictamnosides F and G—Two novel sesqui-terpene diglycosides with -configuration glucose anits from Dictamnus dasycarpus

Weimin Zhao*, Shunchun Wang, Guowei Qui*, Rensheng Xu & Kurt Hostettmann

Two novel sesquiterpene diglycosides named dictamnosides F (1) and G (2) have been isolated from methanol extract of the root burk of Dictamnus dasycarpus. Their structures have been determined on the basis of spectroscopic and chemical analysis. The existence of -configuration glucose units in their structures is not very common in natural glycosidic components.



















751

Demethylacetovanillochromene from Tithonia diversifolia


K M Shamsuddin*, Mohd Asif Musharraf, Md Omair Zobairi & Nazakat Ali

Structure elucidation of a chromene isolated from Tithonia diversifolin as 2,2-dimethyl-2H-(1-hydroxy-6-acetyl)[2,3-b]pyran (Demethylacetovanillochromene) is described.











Authors for correspondence are indicated by (*)





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