Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

Total visitors: 1,559  since 11-12-06

VOL. 45B

NUMBER 12

DECEMBER 2006

CONTENTS

Rapid Communication

2684

Preparation of functionalised tetraphenylmethane derivatives via the Suzuki-Miyaura cross-coupling reaction

 

IPC Code: Int.Cl.8 C07C

A general methodology for the synthesis of various symmetrical and unsymmetrical tetraphenylmethane (TPM) derivatives is reported using the Suzuki-Miyaura (SM) cross-coupling reaction as a key step. The formation of an interesting self-coupling product during the SM cross-coupling reaction of mono-iodo tetraphenylmethane derivative is also observed.

 

 

Sambasivarao Kotha* & Manoranjan Behera

 

 

 

 

 

Papers

 

 

 

2690

A facile [hydroxy(tosyloxy)iodo]benzene mediated synthesis of 2-arylimidazo[1,2-a]pyrimidines and their conversion into 3-bromo-2-arylimidazo[1,2-a]pyrimi­dines

 

IPC Code: Int. Cl.8 C07D

a-Tosyloxyketone 2, obtained through hypervalent iodine oxidation of enolizable ketones using [hydroxy­(tosyloxy)­iodo]benzene (HTIB) in acetonitrile, on treatment with 2-aminopyrimidine 3 generates regioselectively 2-arylimi­dazo[1,2-a]pyrimidine 6 which upon subsequent treatment with bromine undergoes electrophilic substitution at position-3 to yield 3-bromo-2-arylimidazo[1,2-a]pyrimidine 8.

 

 

Ranjana Aggarwal* & Garima Sumran

 

 

 

 

 

 

 

 

 

 

 

 

 

2696

Synthesis of 3-amino-2-methyl/ethyl-5,6,7,8-tetrahydro­[1]­benzothieno[2,3-d] pyrimidin-4(3H)-one and its Schiff bases as possible antimicrobial and non-steroidal antiinflammatory agents

 

IPC Code: Int.Cl.8 C07D

 Hitherto unreported 3-amino-2-methyl-5, 6,7,8-tetra­hydro­[1]benzothieno[2,3-d]pyrimid-4 (3H)-one 3a and 3-amino-2-ethyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimid-4 (3H)-one 3b are prepared and treated with aromatic aldehydes to get Schiff bases 4a-l and 5a-l. The newly synthesized compounds are characterized by spectral analysis. All the compounds are screened for antibacterial and antifungal activity. Eight compounds are screened for their anti-inflammatory activity. A few of the compounds exhibit promising biological activity.

 

 

B Narayana*, B V Ashalatha, K K Vijaya Raj & N Suchetha Kumari

 

 

 

 

 

 

2704

New heterocyclic derivatives of 3-formyl-4-hydroxy­coumarin

 

IPC Code: Int.Cl.8 C07D

The reaction of 4-hydroxy-2-oxo-2H-[1]benzopyran-3-carboxaldehyde with active methylene compounds under mild conditions results in the formation of 3, 6 and 9. The polyketomethylene compound 3 has been converted to pyrazoles 4a,b and isoxazole 4c by treatment with hydrazine, phenylhydrazine and hydroxylamine.

 

 

 

zeba N Siddiqui* & Mohammad Asad

 

 

 

 

 

 

 

 

 

 

 

 

 

2710

Diastereoselective synthesis of 1,3-disubstituted 1,2,3,4-tetrahydro-b-carbolines using Pictet-Spengler reaction in non-acidic aprotic media

 

IPC: Int.Cl.8 C07D

Studies on the use of Pictet-Spengler reaction in non-acidic aprotic media for the diastereoselective synthesis of some tetrahydro-b-carbolines are reported.

 

 

S D Sharma*, Susmita Bhaduri & Gurpreet Kaur

 

 

 

 

 

 

 

2716

An expeditious synthesis of 1,5-benzodiazepine derivatives catalyzed by CdCl2

 

IPC Code: Int.Cl.8 C07D

2,3-Dihydro-1H-1,5-benzodiazepines have been synthesized by the condensation of o-phenylenediamine and cyclic or acyclic ketones in the presence of CdCl2 as catalyst at
80–85şC temperature. The yields are high and the reactions go to completion within 10–20 min.

 

 

M A Pasha* & V P Jayashankara

 

 

 

 

 

 

 

2720

Competing A1,3-strain and Ph:Ph diaxial repulsion in oximes and semicarbazones of N-nitroso-r-2,c-6-diphenylpiperidin-4-ones

 

IPC Code: Int.Cl.8 C07D

The configurations and preferred conformations of oximes 14-18 and semicarbazones 19-22 N-nitroso r-2,c-6-diphenylpiperidin-4-ones have been studied using NMR spectra and semiempirical MO calculations. The nitrosamines 14-22 are found to prefer twist-boat conformations.

 

 

 

 

R Vijayalakshmi, M Muthukumar, S Ponnuswamy*  & R Jeyaraman

 

 

 

 

 

 

 

 

 

 

 

 

 

2736

An enantiospecific strategy to all four diastereomers of A-ring enyne synthon of 1a,25-dihydroxyvitamin D3

 

IPC Code: Int Cl.8 C07C

Enantiospecific syntheses of all the four diastereomers of the A-ring enyne synthon of 1,25-dihydroxyvitamin D3 is described.

 

 

A Srikrishna*, Santosh J Gharpure & P Praveen Kumar

 

 

 

 

 

Notes

 

 

 

2745

Synthesis, antibacterial and antifungal activity of some new pyrido quinazolones

 

IPC Code: Int.Cl.8 C07D

 

 

 

V K Singh & V K Pandey*

 

 

 

 

 

 

 

2749

Montmorillonite K10 clay catalyzed Friedlander synthesis of 1,8-naphthyridines in dry media under microwave irradiation

 

IPC Code: Int.Cl.8 C 07 D

1,8-Naphthyridines 3 are prepared expeditiously in a solventless operation by microwave thermolysis of 2-aminonicotinaldehyde 1 and carbonyl compounds containing a-methylene group 2 in the presence of benign reagent, montmorillonite K10 clay.

 

 

K Mogilaiah* & B Sakram

 

 

 

 

 

 

 

 

 

 

 

 

 

2751

Kinetics of elimination reactions of 1-chloro-1-(4-methoxyphenyl)-2-phenylethane in acetonitrile

 

IPC Code: Int.Cl.8 C07D

Dehydrochlorination of 1-chloro-1-(4-methoxyphenyl)-2-phenylethane in acetonitrile follow unimolecular mechanism. The mass law effect and special salt effect observed confirm the E1 mechanism.

 

 

D Santhosh Kumar & S Balachandran*

 

 

 

 

 

 

 

2754

Microwave promoted efficient synthesis of 2,5-disubstituted 1,3,4-thiadiazole

 

IPC Code: Int Cl8. C07D

A rapid and efficient method for the synthesis of substituted 1,3,4-thiadiazoles is described. The products have been characterized by analytical and spectral (IR and 1H NMR) data.

 

 

Tai-Bao Wei, Hong Liu, Jing-Han Hu, Man-Lin Li, Wei-Xia Xu, Li-Zi Yang & You-Ming Zhang*

 

 

 

 

 

 

 

2757

Total synthesis of antibacterial dibromotyrosine derived alkaloid purpuramine-K

 

IPC Code: Int.Cl.8 C07C

 

 

 

S Malla Reddy, M Srinivasulu & Y Venkateswarlu*

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

2763

QSAR studies of 2,3-diarylpyrazolo[1,5-b]pyridazine analogs as cyclooxygenase-2 inhibitors

 

IPC Code: Int.Cl.8 C07D

 

2D-QSAR analysis study has revealed that the substitution of hydrophobic group in the 2,3-diaryl-pyrazolo[1,5-b] pyridazines at R2 position is favorable while substitution of bulkier group at R2 position is unfavorable for COX-2 inhibitory activity. In 3D-model, Mor14u and Mor29v are 3D-MoRSE code which have been calculated by summing atom weights viewed by a different angular scattering function contributed positively while G (O..O) is a conformational dependent descriptor and based on the geometry of the molecule contributed negatively to COX-2 inhibitory activity.

 

 

 

 

 

 

 

 

 

 

S Revathi, Arun Kumar Gupta, Love Kumar Soni,
S Kavitha, R Wagh & S G Kaskhedikar*

 

 

 

 

 

 

 

2770

Electroreductive generation of (S)-(+)-N,N-dimethyl-2-(hydroxymethyl)-pyrrolidinium mercury compound for enantioselective synthesis of 2-amino-1-alkyl/aryl ethanols

 

IPC Code: Int.Cl.8C07D

(S)-(+)-N,N-Dimethyl-2-(hydroxymethyl)-pyrrolidinium (DMHP+)-mercury compound mediated enantioselective reduction of aminomethyl alkyl/aryl ketones in dimethyl­formamide-2-propanol (9:1) has been carried out using tetrabutylammonium tetrafluoroborate as a supporting electrolyte. The products viz. 2-amino-1-alkyl/aryl ethanols have been obtained in good yield (68-92%) with 35-91% optical purity and have been assigned (S)-configuration.

 

 

 

 

Ashok K Yadav* & Meera Manju

 

 

 

 

 

 

 

2773

A high amylose starch isolated from the tubers of Curcuma aeruginosa

 

IPC Code: Int Cl8.A61K

NMR spectra of the starch, isolated from Curcuma aeruginosa in dimethyl sulphoxide-d6, contain groups of minor 13C, 1H, or O1H signals attributable to glycosyl end groups and the absence of other residues associated with branching in amylopectin molecules. 13C and 1H NMR spectral studies show that it is a high amylose starch. X-ray diffraction study reveal b-type polymorphic forms characteristic of high amylose starch.

 

 

 

 

C E Ranjini* & K K Vijayan

 

 

 

 

 

 

 

 

 

 

 

 

 

2776

Conventional and ultrasound mediated synthesis of some thiadiazoles, triazoles and oxadiazoles

 

IPC Code: Int.Cl.8 C 07 D

Acid hydrazide 1 when treated with aryl isothiocyanates gave the compounds 2. These compounds 2 in acidic medium gave compounds 3 i.e. thiadiazoles and in basic medium gave compounds 4 i.e. triazoles. Compound 2 on treatment with I2/KI in NaOH gave compound 5 i.e. oxadiazoles.

 

 

S K Narwade, V B Halnor, N R Dalvi, C H Gill &

B K Karale*

 

 

 

 

 

 

 

2781

New method for the synthesis of 1,3,5-triarylbenzenes

 

IPC Code: Int.Cl.8 C07D

Adsorbed on clayfen together with p-toluenesulfonic acid and catalytic amount of tin tetrachloride anhydrous (5%), aryl ketones are readily turned to 1, 3, 5 –triarylbenzenes in good yields upon exposure to microwaves under solvent-free conditions. A new method for the synthesis of poly substituted benzene is developed, which is simple and rapid.

 

 

 

 

Xiaobi Jing*, Feng Xu, Qihua Zhu, Xinfeng RenDong Li, Chaoguo Yan & Yaocheng Shi

 

 

 

 

 

 

 

2784

Annual Index

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int.Cl8.: International Classification, 8th Edition, 2006