Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

VOLUME 44 B

NUMBER 9

SEPTEMBER 2005


Total visitors: 2,278  since 22-09-05

 

CONTENTS

Papers

 

 

 

1853

N-Fmoc-peptide azides: Synthesis, isolation, characterization and utility in the extension of peptide chains

 

IPC: Int.Cl.7 C 07 K

The synthesis of N-Fmoc-peptide azides employing acid chloride as well as mixed anhydrides has been described. All the peptide azides made have been isolated as solids and characterized. Their use in the extention of the peptide chain from N to C terminal end extension has been described.

 

 

 

 

Vommina V Suresh Babu*, Ganga-Ramu Vasanthakumar &

 Basanagoud S Patil

 

 

 

 

 

 

1859

Synthesis of some novel N-(2-benzothiazolyl)-1-methyl-1-(4-O-β-d-glucopyranosyloxy­phenyl)­azo­methines

 

IPC: Int.Cl.7 C 07 D

An efficient method for glucosylation of hydroxy-azomethines of benzothiazoles without using heavy metal salts has been reported.

 

 

 

 

 

V N Ingle*, U G Upadhyay & S T Kharche

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1863

Synthesis of some 3-phenyl-4-methyl-6-(6-styryl-4-arylpyridin-2-yl)-, 6-(4-styryl-6-arylpyridin-2-yl)- and 6-(4-aryl-8-aryledine-5,6,7,8-tetrahydro­quino­lin-2-yl)coumarins

 

IPC: Int.Cl.7 C 07 D

Various 3-phenyl-4-methyl-6-(6-styryl-4-arylpyridin-2-yl)- 7a-f, 6-(4-styryl-6-aryl-pyridin-2-yl)- 8a-f and 6-(4-aryl-8-aryledine-5, 6, 7,8-tetrahydroquinolin-2-yl)­coumarins  9a-f have been synthesized by reacting 3-phenyl-4-methyl-6-coumarinoylmethylpyridinium bro­mide 3 with  a,b-unsaturated ketones 4a-f, 5a-f and 6a-f, respectively under Kroehnke’s reaction condition.

 

 

 

 

D I Brahmbhatt*, V P Pandya, C N Patel &

M A Patel

 

 

 

 

 

 

 

1868

Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities

 

IPC: Int.Cl.7 C 07 D 215/00

The regioselective synthesis of 2-chloro-3-formyl-quinolines 2a-k from the reaction of N-arylacetamides 1a-k with Vilsmeier-Haack re­agent is reported.

 

 

 

 

Ambika Srivastava & R M Singh*

 

 

 

 

 

 

 

1876

Beckmann rearrangement of ketoximes and deprotection of  aldoximes in solvent-free conditions

 

IPC: Int.Cl.7 C 07 C 251/32

hosphoric acid is an efficient and mild eagent for regeneration of aldehydes from oximes, but ketoximes are converted to amides or lactams by Beckmann rearrangement. The reactions are carried out in solvent- free condition nder microwave irradiation.

 

 

 

Krishna Banerjee* & Alok Kumar Mitra

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

1880

Synthesis, antifungal, antitumor and anti-inflammatory activities of some new 5-substituted arylimino-3-(2,4-diethoxyarylimino)-1, 2, 4-dithia­zolidines

 

IPC: Int.Cl.7 C 07 D 285/00 // A 61 P 31/10, 29/00

Synthesis, characterization, antifungal, antitumor and antiinflammatory activity of 1,2,4-dithiazolidine derivatives

 

 

Paresh Manna*, (late) R Singh, K K Narang &

S K Manna

 

 

 

 

 

 

 

1887

Novel fluoro substituted benzo[b]pyran with anti-lung cancer activity

 

IPC: Int.Cl.7 C 07 D // A 61 P 35/00

6-Fluorobenzo[b]pyran-4-one 1 on condensation with aromatic aldehydes yield 3-arylmethylene-6-fluoro-2,3-dihydrobenzo[b]pyran-4-ones 2. Both are subjected to the action of different reagents to afford new products 3-12. The synthesized compounds have been tested against three cell lines of human cancer (lung, breast and CNS cancer), and these compounds show anticancer activity at low concentration as compared to reference drug 5-fluorodeoxyuridine.

 

 

Abou El-Fotooh G Hammam*, Osama I Abd El-Salam,

Ashraf M Mohamed & Nagla Abdel Hafez

 

 

 

 

 

 

1894

Nitrogen ligands: The transition metal catalyzed reaction of aryl halides with olefins (Mizoroki-Heck), phenylboronic acid (Suzuki coupling) and Buchwald-Hartwig amination; the new catalysts and the effect of co-catalysts: Aryl halide activation ¾ Part I

 

IPC: Int.Cl.7 C 07 C, C 07 D

 

 

 

Suresh Iyer*, Girish M Kulkarni, C Ramesh & Aruna K Sattar

 

 

 

 

 

 

 

 

 

1909

Kinetics and mechanism of the oxidation of some a-amino acids by benzyltrimethylammonium tribromide

 

IPC: Int.Cl.7 C 07 B 33/00, C 07 C 211/00

 

The oxidation of a-amino acids by  benzyltrimethyl­ammonium tribromide, in aqueous acetic acid, leads to the formation of the corresponding aldehydes via an intermediate formation.

 

 

 

Dimple Garg & Seema Kothari*

 

 

 

 

 

 

 

1915

Biologically active inositol, sterols and lipid derivatives from Sesbania bispinosa

 

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

Fatty acids, poriferasterol, its glucoside, pinitol along with following new lipid derivatives 2- 7 have been isolated from the hexane and methanol extracts of leaves, stems and roots of Sesbania bispinosa.

 

 

 

Laxminarain Misra & Shahzad A Siddiqi*

 

 

 

 

 

 

 

 

1922

Composition of a new chemotype of Tanacetum nubigenum

 

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

 

Six compounds have been isolated from Tanacetum nubigenum Wall of North Western Himalaya. (3R,6R)-Linalool oxide acetate 1 (69.37%) is being reported for the first time, which marked it as a new chemotype. Other important compounds are 2-hydroxy-4,6-dimethoxyacetophenone 2, (E)- 2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4,4]non-3-ene 3,  (Z)- 2-(2,4-hexadiynylidene)-1,6-dioxaspiro[4,4]non-3-ene 4,  ß-eudesmol 5 and selin-11-en-4a-ol 6.

 

 

C S Chanotiya, S S Sammal & C S Mathela*

 

 

 

 

 

Notes

 

 

 

1927

Synthesis of 5-(D2-5'-aryl-3'-isoxazolyl)-3,6-dimethyl­isoxazolo[4,5-b]pyridines

 

IPC: Int.Cl.7 C 07 D

Isoxazolopyridine-N-oxides 2 are deoxygenated to pyridines 3 by treatment with PCl3.  5-Acetyl-3,6-dimethylisoxazolo[4,5-b]pyridine 3 is condensed with aromatic aldehydes to give a, b-unsaturated carbonyl moiety at position-5, which then cyclizes to isoxazole ring by reaction with hydroxylamine hydrochloride in sodium acetate-acetic acid to result title compounds 7.

 

 

 

E Rajanarendar*, M Srinivas, P Ramesh &

K Ramu

 

 

 

 

 

 

 

1931

Microwave induced solvent – free synthesis of
1-aryl-2-(1E)-arylvinyl-4-arylmethylene-2-imida­zolin-5-ones

 

IPC: Int.Cl.7 C 07 D

A microwave – assisted synthesis of the title compounds under solvent-free conditions is described. The yields and reaction time period are noticeably improved in comparison with conventional methods.

 

 

T Venkata Maruthikumar, V Prabhakar Reddy & P Hanumantha Rao*

 

 

 

 

 

 

 

 

1933

Synthesis and antimicrobial activity of some succinimides

 

IPC: Int.Cl.7 C 07 C // A 61 P 31/04

A series of substituted succinimides 3 are prepared from hydrazides and maleimides. The compounds are characterized and screened for their antimicrobial activities.

 

 

 

 

 

 

 

 

 

N P Shetgiri* & B K Nayak

 

 

 

 

 

 

 

1937

Synthesis of some isatin based novel spiroheterocycles and their biological activity studies

 

IPC: Int.Cl.7 C 07 D 209/04 // A 61 P 31/10

Some new 1-{3'-(substituted phenyl)-spiro[3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione-1'-ylacetamido}-2-phe­nyl-4-arylidine-5-oxoimidazolines have been pre­pared by reacting 3'-(substituted phenyl)-spiro[3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione-1-ylacetyl­ hydra­­zine with various azalactones. They have been evaluated for their antibacterial activity.

 

 

 

 

 

 

 

 

 

Uday C Mashelkar* & Deepak M Rane

 

 

 

 

 

 

 

 

 

1940

Synthesis and characterisation of isoquinolinyl quinazolines and a study of their antiviral and antifungal activities

 

IPC: Int.Cl.7 C 07 D 215/00 //A 61 P 31/10, 31/12

An approach to develop new isoquinolinyl quina­zole for studying their antiviral and anti­fungal activities.

 

 

 

 

V K Pandey*, L P Pathak  & S K Mishra

 

 

 

 

 

 

 

1944

Synthesis, characterization and anti-bacterial activity of some new 2,3,6-trisubstituted quina­zolin-4(3H)-ones

 

IPC: Int.Cl.7 C 07 D 215/00 // A 61 P 31/04

Some new 2,3,6-trisubstituted quinazolin-4(3H)-ones 5 have been synthesized by Ullmann condensation of substituted anthranilic acids 4 and substituted benzothiazolylquinazolines 3, which are synthesized by condensation of 6-bromo-2-substituted quinazolin-4(3H)-one 1 and various substituted 2-amino­benzo­thiazoles 2 in the presence of pyridine. All the compounds in this series have been screened for their antibacterial activity.

 

 

 

 

Rohit D Patel, Manish P Patel*& Ranjan G Patel

 

 

 

 

 

 

 

1947

A simple conversion of E-3-benzylidene­flavanones to 3-benzoylflavones by chromic acid oxidation

 

IPC: Int.Cl.7 C 07 D 311/30

Oxidation of E-3-benzylideneflavanones with CrO3/ AcOH yields 3-benzoylflavones in moderate yield.

 

 

 

 

 

Asok K Mallik*  & Falguni Chattopadhyay

 

 

 

 

 

 

 

 

1950

Direct esterification of carboxylic acids with p-cresol catalysed by acid activated Indian bentonite

 

IPC: Int.Cl.7 C 07 C

Acid activated Indian bentonite catalyst is used for the first time to esterify various carboxylic acids with p-cresol in average to excellent yields.

 

 

 

 

 

 

B Vijayakumar, Pushpa Iyengar,

Gopalpur Nagendrappa* & B S Jai Prakash*

 

 

 

 

 

 

 

1954

Improved and efficient conversion of nitriles using Na2CO3/SOCl2

 

IPC: Int.Cl.7 C 07 C

An efficient conversion of aldoximes into nitriles occur with Na2CO3/SOCl2   in CH2Cl2.Acceleration of reaction rate,  simple work-up and formation of clean  products are remarkable features of this  method.

 

 

 

 

 

 

F Kazemi *, A R Kiasat* & M Javeherian

 

 

 

 

 

 

 

1957

Phase transfer catalyzed synthesis under ultrasonic irradiation and bioactivity of N ¢-(4, 6-disubstituted-pyrimidin-2-yl)-N-(5-aryl-2-furoyl)­thiourea derivatives

 

IPC: Int.Cl.7 C 07 D

Ten new N¢-(4,6-disubstituted-pyrimidin-2-yl) -N-(5-aryl-2-furoyl)thioureas have been synthesized using PEG-400 as solid-liquid phase transfer catalyst under ultrasonic irradiation.

 

 

 

 

Shao-Yong Ke*, Tai-Bao Wei, Si-Jia Xue,

Li-Ping Duan & Jing-Zhi Li

 

 

 

 

 

 

 

 

1961

Lipase catalyzed kinetic resolution of a-phenyl-2-nitroalcohols

 

IPC: Int.Cl.7 C 07 C

It has been demonstrated that optically pure (S)-a-phenyl-2-nitroalcohols can be efficiently prepared by kinetic resolution of the corresponding 2-nitroalcohols involving amano lipase from Pseudomonas fluorescens . In the case of b-phenyl-2-nitroalcohols, the corresponding (R)-acetates are also obtained in good optical and chemical yield along with the (S)-alcohols.

 

 

 

 

 

 

 

 

Jagat C Borah, Joshodeep Boruwa,

Biswajit Kalita, Ajit K Hazarika &

Nabin C Barua*

 

 

 

 

 

 

 

1966

Two new flavonoids from Andrographis macrobotrys

 

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

Two new flavonoids, 5,7,8,2¢ - tetramethoxyflavanone 1 and 2¢-hydroxy-2,3,4¢ - trimethoxychalcone 3, together with three known flavones, 5-hydroxy-7-methoxy­flavone 2, 5,2¢,6¢-trihydroxy-7-methoxyflavone 4 and 5,7,2¢,6¢-tetrahydroxyflavone 5 have been isolated from the whole plant of Andrographis macrobotrys. The structures of the new compounds 1 and 3 have been established by extensive 2D NMR and ESI-MS/MS studies.

 

 

 

B Anil Kumar Reddy, M Vijaya Bhaskar Reddy,
D Gunasekar*, M Marthanda Murthy, C Caux & B Bodo

 

 

 

 

 

 

1970

Anthraquinone glycoside from stem bark, fatty acids and sterols from seeds of Cassia reingera

 

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

From the bark of Cassia reingera 1,5,6-trihydroxy-3-methylanthraquinone-8-O-a-l-glucoside has been isolated and its structure elucidated with the help of chemical studies and spectral data. The dyeing property of crude anthraquinone has been studied to develop variety of shades on wool by using different mordants. Sterols and fatty acids have been isolated from the seeds of Cassia reingera and are identified by using GLC techniques by comparison with authentic sample

 

 

 

 

Lalita Ledwani & Mukhtar Singh*

 

 

 

 

 

Announcements

1972

Second International Symposium On Green/ Sustainable Chemistry

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl.: International Classification, 7th Edition, 1999