Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

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Special Issue on Recent Developments in Heterocyclic Chemistry

VOL. 47B

NUMBER 7

July 2008

CONTENTS

Papers

 

 

 

1063

A facile synthesis of novel triazabicyclic molecules as potential bicyclic templates for pharmaceutical ligands by the ring opening metathesis-cross metathesis of triazatricyclo[3.2.1.02,6]dec-8-ene-3,5-diones

 

Novel multifunctional triazabicyclic molecules are synthesized in excellent yields by the ring opening metathesis-cross metathesis of triazatricyclo [3.2.1.02,6]dec-8-ene-3,5-diones with various terminal olefins. The rigid synthesized molecules can be used as potential bicyclic templates for a number of pharmaceutically important ligands.

 

 

 

Saithalavi Anas, Chechattil Sarika,

Rani Rajan & K V Radhakrishnan*

 

 

 

 

 

 

 

 

1071

Synthesis of novel heterocyclic calixarenes via the Diels-Alder reaction of calix[4]bis(spirodienones)

 

Calix[4]arene derived bis(spirodienone) can elicit diverse modes of cycloaddition by acting as both dienophile and diene in its cycloaddition with 1,2- and 1,4-benzoquinones.  The experimental results leading to different cycloadducts have been rationalized on the basis of theoretical calculations.

 

 

 

V B Ganga, E Suresh, C H Suresh &
R Luxmi Varma*

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1080

A convenient procedure for the synthesis of racemic syn-1,2-diarylethane-1,2-diols by osmate catalyzed dihydroxylation of trans-stilbenes facilitated byTröger base

 

Racemic (d,l) mixture of syn-1,2-diarylethane-1,2-diols are prepared from the corresponding substituted trans-stilbenes by osmate catalyzed dihydroxylation facilitated by racemic Tröger base under ambient conditions.

 

 

 

 

 

 

 

 

 

 

 

Sakilam Satishkumar & Mariappan Periasamy*

 

 

 

 

 

 

 

1084

Hantzsch synthesis of polyhydroquinolines - A simple,  efficient and neat protocol

 

A variety of polyhydroquinolines have been synthesized under eco-benign conditions. The reaction proceeds smoothly without any catalyst at room temperature in short reaction time. The yields and purity are excellent.

 

 

 

 

Pandurangan Arumugam &
Paramasivan T Perumal*

 

 

 

 

 

 

1091

Cu(OTf)2 catalyzed Biginelli type condensation of aldehydes, β-keto esters and carbamates: Synthe­sis of  3,4-dihydro[1,3]oxazin-2-ones

 

 

 

 

 

 

 

 

 

 

 

 

Arun R Jagdale, Abhimanyu S Paraskar
& Arumugam Sudalai*

 

 

 

 

 

 

 

 

 

 

 

1096

Facile synthesis of alkoxyphthalimide derivatized benzimidazole assembled pyrazoles, pyrimidines and isoxazoles, via common intermediate chalcone

 

Some 2-(3-aryl-2-phenyl-3,4-dihydropyrazol-5-yl)-1-N-alkoxy­phthalimidobenzimidazole 9a-h, 4-(1-N-alkoxy­phthali­midobenzimidazol-2-yl)-6-arylpyrimidin-2-amine 10a-h, 2-(5-aryl-4,5-dihydroisoxazol-3-yl)-1-N-alkoxy­ph­thali­midobenzimidazole 11a-h have been synthesized by two alternative reaction routes. Synthesized compounds have been characterized by analytical and spectral studies.

 

 

Archita Bapna, Swati Ojha & G L Talesara*

 

 

 

 

 

 

1108

A task specific basic ionic liquid, [bmIm]OH-promoted efficient, green and one-pot synthesis of tetrahydrobenzo[b]pyran derivatives

 

An efficient method for the synthesis of a variety of 4H-benzo[b]pyran derivatives by a one-pot three component condensation of aldehydes, cyclohexa-1,3-diones and malononitrile/ethyl cyano acetate has been developed using an ionic liquid, [bmIm]OH at room temperature under organic solvent free conditions.

 

 

 

Brindaban C Ranu*, Subhash Banerjee & Sudeshna Roy

 

 

 

 

 

 

 

 

 

 

 

 

 

1113

Synthesis of highly functionalised linear penta­cyclic compounds from Baylis-Hillman adduct of heteroaldehydes with azomethine ylides via [3+2] cycloaddition

 

Montmorillonite K10 clay promoted one-pot synthesis of penta- and tetracyclic systems from Baylis-Hillman adduct of heteroaldehydes with azomethine ylides generated from ninhydrin and proline or sarcosine via [3+2] cycloaddition is reported. 

 

 

 

 

 

Ponnusamy Shanmugam*, Suchithra Madhavan, Baby Viswambharan & Vadivel Vaithiyanathan

 

 

 

 

 

 

 

 

1117

A facile synthesis of novel dispiroindano thiazolo[2,3-b]benzo[h]quinazoline pyrrolidines through 1,3-dipolar cycloaddition reaction

 

 

 

 

 

S Kathiravan & R Raghunathan*

 

 

 

 

 

 

 

 

1120

Design and synthesis of spiro-heterocycles by ring-closing metathesis

 

 

 

 

 

 

Sambasivarao Kotha* & Ashoke Chandra Deb

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1135

Synthesis and QSAR studies of 4-oxo-thiazolidines and 2-oxo-azetidines as potential antibacterial agents

 

Several 2-(4-chlorophenyl)-N-(4-oxo-2-aryl(l,3,thiazolidin-3-yl))acetamides 2, N-[3-chloro-4-(2-aryl)-2-oxo-azeti­din­yl]-2-(4-chlorophenyl)acetamides 3, N-(4-oxo-2-aryl(1,3,-thia­diazolidin-3-yl){4-[5-oxo-2-phenyl-4-(phenyl­methyl­ene)­­­­­­­­­(2-imidazolinyl) phenyl} carboxamides 7 and N-(3-chloro-2-oxo-4-arylazetidinyl){4-[5-oxo-2-phenyl-4-(phe­n­yl­methylene)(2-imidazolinyl)]phenyl}carboxamides 8 have been synthesised and evaluated for their antibacterial activity. The QSAR studies of the new bio-active molecules have been carried out by Hansch’s LFER method.

 

 

 

N C Desai*, M D Shah, A M Bhavsar & A K Saxena

 

 

 

 

 

Notes

 

 

 

1145

Synthesis and cytotoxicity studies of thiazole analogs of the anticancer marine alkaloid dendrodoine

 

The synthesis and cytotoxicity evaluation of 2-N,N-dimethylamino-5-indol-3-oylthiazole and its other 5-hetaroyl derivatives 2a-h as members of a novel portfolio of the thiazole analogs of the cytotoxic marine alkaloid dendrodoine (3-N,N-dimethylamino-5-indol-3-oyl-1,2,4-thiadiazole) 1 is reported.

 

 

 

T F Abbs Fen Reji, S K C Devi,  K  K Thomas, K  G  Sreejalekshmi, S  L  Manju, M  Francis
S K Philip, A Bharathan & K N Rajasekharan
*

 

 

 

 

 

 

 

 

 

 

1151

Dynamic 1H NMR study of rotational energy barrier around the aryl-nitrogen single bond in γ-spiroiminolactones derived from reaction between 2,6-dimethylphenyl isocyanide and dialkyl acetylenedicarboxylates in the presence of phendione

 

The free-energy of the activation (ΔG) for restricted rotation around the aryl-nitrogen single bonds in γ-spiroiminolactones has been calculated by dynamic 1H NMR studies.

 

 

 

 

 

 

 

 

 

 

 

 

Malek Taher Maghsoodlou*, Ghasem Marandi, Sayyed Mostafa Habibi Khorassani,
Lotfali Saghatforoush, Ali Aminkhani &
Roya Kabiri

 

 

 

 

 

 

 

 

1154

A mild, efficient and one-pot synthesis of 2-substituted benzimidazoles by ZrOCl2.8H2O catalyzed ring closure reaction

 

A mild, efficient and one-pot synthesis of an array of
2-substituted benzimidazoles from an appropriate
o-phenylenediamine and orthoesters such as orthoformate, orthoacetate and orthovalerate using ZrOCl2.8H2O at room temperature and under microwave irradiation is described. Eco-friendly, solvent-free methodology has been employed under microwave condition. Compared with the conventional method, microwave irradiation method has the advantages of excellent yields (81-93%) and shorter reaction time (5-10 min).

 

 

 

 

 

 

 

 

Ch Sanjeeva Reddy* & A Nagaraj

 

 

 

 

 

 

 

 

 

 

 

 

 

1160

MgCl2·6H2O/p-TSA catalyzed simple and efficient synthesis of some known and novel quinolines

 

A simple and an efficient method has been developed for the condensation of o-aminoaryl ketones with α-methylene ketones in the presence of catalytic amounts of MgCl2·6H2O/p-TSA to afford the corresponding fused cyclic quinolines in high yield using the Friedlander heteroannulation reaction. The reaction works at ambient temperature to give the products within 40 min.

 

 

 

M A Pasha* ,V P Jayashankara & K A  Mahammed

 

 

 

 

 

 

Authors for correspondence are indicated by (*)