Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 41B

NUMBER 3

MARCH 2002

CONTENTS

 

Rapid Communications

 

583

InCl3-an efficient Lewis acid catalyst for stereoselective O-glycosidation reaction

InCl3 catalysed O-glycosidation of acetobromo glucose and 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-a-d-manno-pyranosyl bromide with different aliphatic alcohols proceed with high yield and anomeric selectivity.

 

 

 

Rina Ghosh*, Arijit Chakraborty, Dilip K Maiti & Swaraj B Maiti

 

 

 

 

Papers

 

 

 

586

Nucleophilic reaction of glycidol tosylate and the corresponding cyclic sulfate with various nucleophiles: A comparative study

The nucleophilic reaction of glycidol tosylate and its corresponding cyclic sulfate tosylate with various nucleophiles have been carried out with the view to study the possible mode of attack by nucleophiles at C1, C2 or C3 positions of substrate. Under similar conditions cyclic sulfate 2 shows better regioselectivity and better reactivity than its corresponding epoxide tosylate 1 derivatives.

 

 

B B Lohray*, B M Rajesh & V Bhushan

 

 

 

 

 

 

 

 

 

 

593

Synthesis of chiral 3-acyl-4-alkylthiazolidine-2-thiones as enantioselective acylating agents

Chiral acylating agents 4a,b are useful for enantioselective acyl transfer to racemic amines and amino acids in 78-94% yield and 48-68% ee.

 

 

 

L D S Yadav* & Suman Dubey

 

 

 

 

 

 

 

596

One-pot synthesis of dimethyl 8,8-dimethyl-6,10-dioxo- 3 -phyenylspiro[4.5]deca-2-ene-1, 2-dicar-boxylate mediated by vinyltriphenylphosphonium salt

A single-step synthesis of title compound 6 is described.

 

Ali Ramazani* & Ehssan Fotouhi-Ardakani

 

 

 

 

 

 

 

598

Synthesis of C7-C16-alkyl glycosides: Part III  Synthesis of alkyl d-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of b-peracetylated sugar derivative (galactose) with fatty alkanols is used in the synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.

 

 

Stanimir Konstantinović*, Biljana Dimitrijevića & Veselin Radulović

 

 

 

 

 

 

 

 

 

 

604

A newly developed synthesis of 1,3,5-trichlorobenzene (sym. TCB) from aniline

1,3,5-Trichlorobenzene (sym.TCB) has been synthesised by diazotisation of 2,4,6-trichloroaniline (sym.TCA) (by converting aniline into anilinium chloride followed by its chlorination) in the presence of H2SO4/NaNO2 and H3PO2 and its purity has been established by comparing properties of TATB obtained from imported sym.TCB and from laboratory prepared sym.TCB.

 

Mehilal, R B Salunke & J P Agrawal*

 

 

 

 

 

 

608

Synthesis and characterization of new 1-organylsilatranes

 

A series of 1-organylsilatranes, X(CH2)nSi(OCHRCH2)3N 1 have been synthesized in yields ranging from 82 to 95% by transetherification of 1-organyltrialkoxysilanes with trialkanolamines and characterized by elemental analyses, IR, 1H as well as 13C NMR spectroscopy.

 

 

R = H, Me, n = 3, X = -NHCOCH3, -NHCONH2,
2-imidazolinyl, cyanurate; R = H, Me, n = 2,
X = 3,4-epoxycyclohexyl

 

Shailesh C Verma & M Nasim*

 

 

 

 

 

 

 

614

Fast N-CO rotational, equilibria in twist-boat conformations of N-ethoxycarbonyl-r-2,c-6-di-phenylpiperidines

The conformational preferences of N-ethoxycarbonyl-r-2, c-6-diphenylpiperidines has been determined by NMR spectral techniques, X-ray crystallography and semiempirical molecular orbital calculations.

 

 

 

R Jeyaraman*, S Ponnuswamy, M Venkatraj,
M Sureshkumar, D Kumaran &
M N Ponnuswamy

 

 

 

 

 

 

 

 

 

 

628

Condensed bridgehead nitrogen heterocyclic systems: Synthesis and antimicrobial activity of thiazolo-[3,2:2,3]-as-triazino[5,6-b]indoles and isomeric thiazolo[2,3:3,4]-as-triazino[5,6-b]indoles

2, 3-Dihydro -6- ethyl- 5H -as-triazino[5, 6-b]indole-3-thione 4 on condensation with a-haloketone gives 3-aroylmethylthio-6-ethyl- 5H -as-triazino[5, 6-b]indole-hydrobromide 5.

 

Jag Mohan* & Anupama

 

 

 

 

 

 

 

631

Selective reductions of substituted a-(1,2,4-triazol-yl) chalcones with NaBH4 and Al-isopropoxide: Synthesis of substituted ()-a-(4-chlorophenyl)-b-(phenylmethylene)-1H-1,2,4-tri-azole-1-ethanols having potential bacteriostatic and agro-based fungicidal activity

 

 

Vinod Rama Uchil & Vidya Joshi*

 

 

 

 

 

 

 

635

A concise conversion of b-asarone into 1-(3-methoxypropanoyl)-2,4,5-trimethoxybenzene occurring in Cordia alliodora

The first synthesis of 1-(3-methoxypropanoyl)-2,4,5-trimethoxybenzene 4, a natural phenylpropanoid occurring in Cordia alliodora, has been achieved, from b-asarone 1 of Acorus calamus.

 

Arun K Sinha*, Ruchi Dogra &
Bhupendra P Joshi

 

 

 

Notes

 

 

 

639

Synthesis of p-tolyl 3,4-O-isopropylidene-2-O-(methylthiomethyl)-b-d-fucopyranose

Treatment of p-tolyl 3,4-O-isopropylidene-6-deoxy-1-thio-b-d-galactopyranoside and related compounds with methyl sulfoxide in the presence of acetic anhydride afforded the formation of a methylthiomethyl ether namely p-tolyl 3,4-O-isopropylidene-2-O-(methylthiomethyl)-b- d -fucopyranose in place of the expected 2-keto compound.

 

 

 

 

 

Kakali Sarkar & Nirmolendu Roy*

 

 

 

 

 

 

 

642

A palladium catalyzed synthesis of wheel and axle hydrocarbons : strategic use of tetraphenylmethane stoppers

 

 

 

 

 

 

Saumitra Sengupta*, Subir Kumar Sadhukhan & Rajkumar Sunil Singh

 

 

 

 

 

645

An efficient protocol for the reduction of azidocyclodextrins catalyzed by indium

 

 

 

 

L Rajender Reddy, M Arjun Reddy,
N Bhanumathi & K Rama Rao

 

 

 

 

 

 

 

 

 

 

647

The Vilsmeier cyclisation of azides : A novel route towards the synthesis of imidazo[1,2-a]quinazoline-1,5-diones

Imidazo[1,2-a]quinazoline-1,5-diones have been prepared in one pot from 2-azido-N-(2-carboxyaryl)-acetamides.

 

 

 

S Akila, V J Majo & K Balasubramanian*

 

 

 

 

 

 

 

650

Microwave assisted Gould-Jacob reaction: Synthesis of 4-quinolones under solvent free conditions

Microwave irradiated Gould-Jacob reaction between aromatic amines and EMME for the synthesis of 4-quinolones under solvent free conditions is described.

 

 

 

 

Chaitanya G Dave* & Hardik M Joshipura

 

 

 

 

 

 

 

653

Tetrahydroimidazoles - a promising group of expected NSAIDS-their synthesis and anti-inflammatory activity

Eighteen 3-trisubstituted tetrahydroimidazoles have been synthesised and their structures elucidated on the basis of spectral data. Some of these compounds show better anti-inflammatory activity as compared to indomethacin by carrageenin induced paw edema test in rats.

 

 

 

 

 

M S Y Khan* & Gita Chawla

 

 

 

 

 

 

 

664

Synthesis and antifungal activity of 4-substituted-3,7-dimethylpyrazolo[3,4-e][1,2,4]triazine

A convenient synthesis, mass spectral study and antifungal activity of 4-substituted-3,7-dimethylpyrazolo-[3,4-e][1,2,4]triazine is reported.

 

 

 

Ashish Kumar Tewari, Lily Mishra,
H N Verma & Anil Mishra*

 

 

 

 

 

 

 

 

 

 

668

Synthesis, characterization and pharmacological screening of some isatinoid compounds

Schiff bases and hydrazones of substituted isatins have been synthesized and screened for analgesic, anti-inflammatory and antipyretic activity.

 

 

 

S K Sridhar* & A Ramesh

 

 

 

 

 

 

 

673

Synthesis of methyl 2-methoxy-5-hydroxycin-namate, a metabolite of Murraya paniculata

Methyl 2-methoxy-5-hydroxycinnamate 1 is obtained starting from 2 in four steps with an overall yield of 26%.

 

 

 

 

 

P Padmavathi, J Kavitha, R V Kanumuri &
G V Subbaraju*

 

 

 

 

675

A new monoterpenoid-glucoside from Indian Illicium griffithii

A new monoterpenoid‑glucoside isolated from Indian Illicium griffithii fruits has been characterised as p-menth-1(7),4(8)-diene-3-O-b-d-glucoside by spectral data and chemical studies.

 

1 R = Glu

2 R = H

 

 

S K Agarwal*, S S Sammal, Mohd Haneef & Sushil Kumar

 

 

 

 

 

 

 

677

A new nortriterpenoid saponin from Sino-franchetia chinensis Hemsl

3-O-α-l-arabinopyranosyl-30-norhederagenin 28-O-α-l-rhamnopyranosyl(14)-β-d-glucopyranosyl (16)-β-d-glucopyranoside 1, has been isolated from Sinofranchetia chinensis.

 

Xiaohui Yang, Ruijun Ma, Quan Xia,
Runhua Lu, Xiaoning Wei , Hanqing Wang & Jie Kong*

 

 

 

 

Authors for correspondence are indicated by (*)