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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

 

VOLUME 44 B

NUMBER 1

JANUARY 2005

 

 

CONTENTS

 

Papers

 

 

 

115

Synthesis and structural study of 3-anisyl-4-(4'-pyridyl(pyridinium)thieno[2,3-b]thienophenes

 

IPC: Int.Cl.7 C 07 D 333/00

The synthesis of novel donor-acceptor thienothio­phenes is described to probe the presence of charge transfer interaction.

 

 

Sabir H Mashraqui*, Harini Hariharasubrahmanian,

Mohamed Ashraf & Yogesh Sangvikar

 

 

 

 

 

 

121

Design, development and synthesis of a novel labeled PNA monomer incorporated in DNA-hexamer to act as a hybridization probe by FRET

 

IPC: Int.Cl.7 C 07 K

A novel PNA monomer with adenine nucleobase and a modified backbone with charged  and a methylene substituted for  in the linker arm has been synthesized.

 

 

Vibha Shukla, Satyendra Mishra, Geeta Watal & Krishna Misra*

 

 

 

 

 

 

 

130

Synthesis of tetrasaccharide related to the repeating unit of the O-antigen from Shigella boydii type 5 in the form of its tert-butyl ester and 2-(trimethylsilyl)ethyl glycoside

 

IPC: Int.Cl.7 C 07 H 3/06

Starting from d-mannose, d-glucose and l-rhamnose a tetrasaccharide derivative I related to the repeating unit of Shigella boydii type 5 has been synthesized.

 

 

Samarpita Roy, Sujit Kumar Sarkar,

Balaram Mukhopadhyay & Nirmolendu Roy*

 

 

 

 

 

 

 

 

 

 

 

 

137

Synthesis of (R)-4,6-O-pyruvated trisaccharide related to the repeating unit of  the antigen from Shigella dysenteriae type 9 in the form of
its 2-(trimethylsilyl)ethyl glycoside

 

IPC: Int.Cl.7 C 07 H 3/06

Starting from d-galactose, and d-mannose a deb­locked trisaccharide, 2-(trimethylsilyl)ethyl 4,6-O-[(R)-1-methoxycarbonylethylidene]-b-d-galacto­py­r­a­n­­­­o­­syl-(1®4)-b-d-mannopyranosyl-(1®4)-b-d-galact­o­­pyranoside has been synthesized, which is a part of the repeating unit of the O-antigen from Shigella dysenteriae type 9.

 

 

 

 

 

 

Samarpita Roy, Sujit Kumar Sarkar

& Nirmolendu Roy*

 

 

 

 

 

 

 

141

A mild and efficient procedure for the preparation of dimethyl and diallyl acetals of aromatic aldehydes mediated by cerium(IV) ammonium nitrate

 

IPC: Int.Cl.7 C 07 C 47/27

The reaction of aromatic aldehydes with cerium(IV) ammonium nitrate in alcohols to afford the corresponding acetals is described.

 

 

i) CAN, ROH, Na2CO3, Reflux, 45 min.

R = Methyl, Allyl

 

 

 

Vijay Nair*, Roshini Rajan, Lakshmi Balagopal, Latha G Nair, Sindu Ros & Kishor Mohanan

 

 

 

 

 

 

 

144

Selective and clean oxidation of alcohols with benzimidazolium fluorochromate (BIFC) under solvent free conditions

 

IPC: Int.Cl.7 C 07 D 233/54

Benzimidazolium fluorochromate (BIFC) is an efficient and selective oxidant for alcohols under solvent free conditions. This oxidation process is effective, economical and eco-friendly.

 

 

 

 

 

 

V Sivamurugan, G Abraham Rajkumar, Banumathi Arabindoo & V Murugesan*

 

 

 

 

 

 

 

 

 

 

 

 

148

Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method

 

IPC: Int.Cl.7 C 07 D 233/54

The reduction of aldehydes such as 2-butyl-5-chloro-3H-imidazole-5-carbaldehyde and veratraldehyde, which are pharmaceutical key intermediates, have been reduced to alcohols by catalytic hydrogenation method in the presence of magnesium and also oximes are reduced to primary amines successively by magnesium/ammonium formate system, is a large scale feasible and cheaper method. The crystal structure of the product, (2-butyl-5-chloro-3H-imidazole-4-yl)methanol 1 is reported.

 

 

Basappa, B H Doreswamy, M Mahendra,

K Mantelingu, M A Sridhara,

J Shashidhara Prasad & K S Rangappa*

 

 

 

 

 

 

 

152

Synthesis and QSAR of O,O-diaryl O-ethyl phosphorothionates for their fungicidal activity against Rhizoctonia solani and Sclerotium rolfsii

 

IPC: Int.Cl.7 A 61K 35/00 // A 61 P 31/10

A series of O,O-diaryl O-ethyl phosphorothionates has been synthesized, their fungitoxicity against   R. solani and S. rolfsii and quantitative structure activity relationship studied.

 

 

Bijul  Lakshman A & R L Gupta*

 

 

 

 

 

 

 

158

Synthesis, characterization and biological activity of 1,3,4-substituted 2-azetidinones

 

IPC: INT.CL.7 C 07 C 59/54 // A61 P 31/12

 

 

 

V K Pandey*, V D Gupta, Mrinalini Upadhyay, Mridula Upadhyay, V K Singh &
Meenal Tandon

 

 

 

 

 

 

163

Synthesis and fungicidal activity of some 6-aryl-2-(-β-d-glucopyranosyl)-3-oxo-2,3-dihydro-1,3,4-oxadiazolo [3,2-b]-1,2,4,6-thiatriazine-1,1-dioxides

 

IPC: Int.Cl.7 C 07 D 285/00

6-Aryl-2-(β-d-glucopyranosyl)-3-oxo-2, 3-dihydro-1, 3, 4-oxadiazolo[3, 2-b]-1, 2, 4, 6-thiatriazine-1, 1-dioxides 4 have been conveniently prepared from 6-aryl-3-oxo-2, 3-dihydro-1, 3, 4-oxadiazolo[3, 2-b]-1, 2, 4, 6-thiatriazine-1, 1-dioxides 2 by reaction of β-d-1, 2, 3, 4, 6-penta-O-acetylglucopyranose and iodine.

 

 

 

R K Khare*, Alok Kumar Srivastava & H Singh

 

 

 

 

Notes
 

 

 

 

167

Synthesis of N-[2-benzyloxy-5-(2-oxiranyl)­phe­nyl]­formamide: Formal synthesis of formoterol

 

IPC: Int.Cl.7 C 07 C 13/20

Synthesis of N-[2-benzyloxy-5-(2-oxiranyl)phenyl]­formamide 4 from 4-hydroxyacetophenone is described to achieve the formal synthesis of formoterol 1.

 

 

Hari Babu Mereyala* & Kalyani Sambaru

 

 

 

 

 

 

 

170

Synthesis of diastereomerically pure acetals of
1-phenylpropiophenone

 

IPC: Int.Cl.7 C 07 H 3/02

Title synthesis is described.

 

 

Hari Babu Mereyala*, Pathuri Gopal &

Sreeman Kumar Mamidyala

 

 

 

 

 

 

 

173

Synthesis of spiroisoxazoline[5.9¢]anthrone

 

IPC: Int.Cl.7 C 07 C 15/28

Synthesis of novel spiroisoxazolines via 1,3-dipolar cycloaddition is described.

 

 

S Manikandan, S Karthikeyan &

R Raghunathan*

 

 

 

 

 

 

 

 

176

Synthesis of new bis-heteroaryl thiohydrazonates and their in situ rearrangement

 

IPC: Int.Cl.7 C 07 D 249/08

Synthesis of the bis-thiohydrazides 4, via  in situ rearrangement of the bis- thiohydrazonate esters 3 is reported.

 

 

Mosselhi A N  Mosselhi, Magda A Abdallah, Sayed M Riyadh & Ahmad S Shawali*

 

 

 

 

 

 

 

180

Synthesis of 1,3-diaryl-4-cyanopyrazoles from the corresponding aldoximes using dimethyl­formamide - thionylchloride complex

 

IPC: Int.Cl.7 C 07 D 231/02

A mild and convenient method for the synthesis of 1,3-diaryl-4-cyanopyrazoles 4 from the corresponding aldoximes 2 using dimethylformamide-thionyl­chloride complex 3 is reported.

 

 

G Jagath Reddy*, S Sailaja, K Pallavi &

K Srinivasa Rao

 

 

 

 

 

 

 

184

Synthesis of a-bromoalkanones using urea-hydrogen peroxide complex and sodium bromide over silica gel-acetic acid

 

IPC: Int.Cl.7 C 07

a-Bromoalkanones 2 have been synthesized by the reaction of alkanones 1 with UHP-NaBr over SiO2-acetic acid in solvent-free conditions under micro­wave irradiation.

 

 

Satya Paul, Puja Nanda & Rajive Gupta*

 

 

 

 

 

 

 

188

Synthesis of arylketones using Envirocat EPZG catalyst

 

IPC: Int.Cl.7 C 07 C 49/225

A safe and cost effective approach for the synthesis of arylketones by using novel and Envirocat EPZG is reported.

 

 

Sonali Ghatpande & Supriya Mahajan*

 

 

 

 

 

 

 

 

193

Microwave thermolysis: Part IX ¾ A rapid reduction of sulphoxides with NaH2PO2 in dry media

 

IPC: Int.Cl.7 C 07 C 11/06, C07 D

 

 

 

 

 

H M Meshram*, Y S S Ganesh, K Ramesh Babu, B Eeshwaraiah & J S Yadav

 

 

 

 

 

 

 

196

Solvent-free synthesis of 2′,3′,5′-tri-O-acetyl -2,6-dichloropurine nucleoside catalyzed by p-toluene­­­sulfonic acid using microwave

 

IPC: Int.Cl.7 C 07

Starting from tetraacetylribofuranose 1 and 2,6-dichloropurine 2, in the presence of p-toluenesulfonic acid, 2',3',5'-tri-O-acetyl-2,6-dichloropurine nucleo­side 3 has been synthesized in microwave oven for the first time. On comparing with the conventional methods, this method has advantages such as shorter reaction time (4.5min), better yield (83.5%), simple workup and environmental acceptability.

 

 

Text Box: 3

 

Text Box: 1

 

 

 

Guirong Qu* & Qibin Liu

 

 

 

 

 

 

 

198

Amberlyst-15 catalyzed acetylation of hetero­aromatics with acetic anhydride under solvent free conditions

 

IPC: Int.Cl.7 C 07 D 209/04

 

 

 

 

Biswanath Das*, Rammohan Pal,

Joydeep Banerjee, G Mahender, Harish Holla &

K Venkateswarlu

 

 

 

 

 

 

 

 

 

 

 

 

201

A mild and efficient method for the acetylation of alcohols

 

IPC: Int.Cl.7 C 07 C 39/00

The acetylation of alcohols has been carried  out efficiently in the presence of a catalytic  amount of Zr(HSO4)4. All reactions are  performed at room temperature and under  heterogeneous conditions  in good to high  yields.

 

 

F Shirini*, M A Zolfigol & A Safari

 

 

 

 

 

 

 

204

Synthesis of 2-aryl-7-(3-oxo-2H-[1,4]-benzoxazin-6-yl)pyrazolo[1,5-a]pyrimidines as potential COX-2 inhibitors

 

IPC: Int.Cl.7 C 07

A series of 2-aryl-7-(3-oxo-2H-[1,4]-benzoxazin-6-yl)pyrazolo[1,5-a]pyrimidines (8a-d and 9a-d) have been synthesized and evaluated for COX-2 inhibitor activity.

 

 

G Jagath Reddy*, S Sailaja & K Srinivasa Rao, P Reddanna & D Bharat Reddy

 

 

 

 

 

 

 

207

A convenient synthesis of Nabumetone ¾ An anti-inflammatory drug candidate

 

IPC: Int.Cl.7 C 07 C 15/24

A facile and industrially viable approach to Nabumetone, an anti-inflammatory agent, is reported.

 

 

G Srinivasulu, A Raghupathi Reddy,

Ch Nagaraju, P Pratap Reddy &

M Satyanarayana Reddy*

 

 

 

 

 

 

 

209

Chemical examination of the mangrove plant Dalbergia spinosa Roxb

 

IPC: Int.Cl.7 C 07

A new neoflavonoid 1 has been isolated from Dalbergia spinosa Roxb besides known triter­penoids and a neoflavonoid 6.

 

 

A S R Anjaneyulu*, V Lakshmana Rao &

K Sreedhar

 

 

 

 

 

 

212

A minor phenolic alkaloid from Cocculus hirsutus Diels

 

IPC: Int.Cl.7 A 61 K 35/78 // A 61 K 31/05

Chemical investigation of the stems and roots of Cocculus hirsutus Diels (Menispermaceae) has yielded a new phenolic alkaloid corsutine 1 in addition to several previously reported compounds.

 

 

S B Yadav & Vyasji Tripathi*

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.: International Classification 7 edition, 1999