Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 40B

NUMBER 5

MAY 2001

CONTENTS

Papers

 

 

 

357

A convenient method for preparation of 3-phenoxy/thiophenoxy-2(1H)-quinolinones

 

 

 

 

 

 

 

 

 

S Riaz Hashim* & P Tirupathy Reddy

Facile synthesis of 3-phenoxy/thiophenoxy-2(1H)-quinolinones (6,10) from N-(2-acetylphenyl)phenoxy/ thiophenoxy acetamides 5 is reported.

 

 

 

 

 

 

 
361

Structure and reactions of monoanils obtained from 2,3-pyridinediamines

 

 

 

 

 

 

 

 

 

 

 

P K Dubey*, Subhash M Kulkarni &

R Vinod Kumar

The reaction of 2,3-pyridinediamines 1 with aromatic aldehydes results in 2 which on dehydrogenative cyclization yields 4. The reactions of 2 with different reagents have been described.

 

 

 

 

 

 

 
368

Heterocyclic systems containing bridgehead nitrogen atom: Synthesis and biological activity evaluation of s-triazolo[3,4-b][1,3,4]-thiadiazoles, s-triazolo[3,4-b][1,3,4]thiadia-zines and s-triazolo[3¢,4¢:2,3] [1,3,4]thiadia-zino[5,6-b]quinoxaline.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Jag Mohan* & Anupama

The condensation of 3-p-(t-butylphenyl)-4-amino-5-mercapto-s-triazole 1, independently, with chloroacetic acid, a-haloketones, benzoin, 2,3-dichloroquinoxaline, aromatic carboxylic acids and carbon disulfide furnish in one step, the cyclized products, 2, 3, 4, 5, 6 and 7, respectively.

 

 

 

 

 

 

 

 
372

Synthesis of some new 3-(bromophenyl)
isocoumarins and their conversion to (dl)-3,4-dihydroisocoumarins

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Muhammad T Hussain, Nasim H Rama* &

Abdul Malik

3-(Bromophenyl)isocoumarins and (dl)-3-(bromo-phenyl)-3,4-dihydroisocoumarins have been synthesized in good yield.

 

 

 

 

 

 

 

 

 
377

Synthesis of some dihydropyrans by utilizing crotonoyl cyanides as heterodienes in a very mild condition

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Md Abul Hashem*, Nurun Nahar &

Shamsun Naher

The reaction of crotonoyl cyanides 1 and 2 with trimethylethene 3 affords the dihydropyrans 6 and 7, respectively. Similarly the compound 1 with acrolein dimethyl acetal 4  and acrolein diethyl acetal 5 gives the isomeric products 8a/8b and 9a/9b, respectively. The bromo derivative 2 with 5 yields only the cis-10.

 

 

 

 

 

 

 

382

Synthesis of some modified guanosine derivatives

 

 

 

 

 

 

M S Amer*, A M Amer, A F Sayed Ahmed &

W M Farouk

The coupling reactions of 8-bromo-guanosine with diphenylamine, ethylhydrazineformate, serine, proline and glycine have been accomplished.

 

 

 

386

Ultrasound mediated synthesis of a few naturally occurring compounds

 

 

 

 

 

 

 

 

 

Jasvinder Singh*, Jasamrit Kaur,

Sandeep Nayyar, Monica Bhandari &

Goverdhan L Kad

Syntheses of 2-methylheptadecane 1, 14-methylpenta-decan-3-one 2, 6-oxo-1-nonanol 3, 5(Z)-undecenoic acid 4 and 2-tridecanone 5 have been achieved under aqueous ultrasonic conditions in the presence of zinc-copper
couple.

 

 

 

 

 

 

 

 
391

Henry and Knoevenagel type condensation reactions initiated by tetraethylammonium superoxide in aprotic medium

 

 

 

 

 

 

 

 

 

 

 

 

 

Ajay Kumar Shukla, Sundaram Singh &

Krishna Nand Singh*

The present report describes easy condensation of malononitrile/nitromethane with some carbonyl compounds under the mild reaction conditions of tetraethylammonium superoxide.

 

 

 

 

 

 

 

 
394

Flavonoids from the leaves of Quercus dentata

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Ying-Jun Zhou, Sui-Xu Xu*,

Qing-Ming Che & Qi-Shi Sun

Four acylated flavonoid glycosides have been isolated from the leaves of  Quercus dentata Thunb. On the basis of chemical and spectroscopic data, their structures are identified.

 

 

 

 

 

 

 
399

Minor saponins from the sea cucumber Cucumaria frondosa

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Nurettin Yayh

The structures of three saponins, frondoside F 5, E1 6 and E2 7 from Cucumaria frondosa  have been determined principally by highfield 1D, 2D NMR data and FAB-MS.

 

 

 

 

 

 

 

 
405

A new glycolipid and a new monohydroxy sterol from Cladiella species of Andaman and Nicobar Islands

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

V Anjaneyulu*, P V Subba Rao, P Radhika,

H Laatsch & R N Asolkar

The isolation of a new monohydroxysterol namely, 4a,23-dimethyl-24-ethyl-cholestane-3b-ol 1 and a new glycolipid namely 2-hydroxy-3-(octadecyloxy)propyl-
b-d-arabinopyranoside 4 are reported from Cladiella  species of the Andaman and Nicobar Islands.

 

 

 

 

Notes

 

 

 

 
410

Temperature controlled stereoscpecific epoxidation of 5-adrosten-3b,17b-diol diacetate. Preparation of 6a and 6b-substituted androstane derivatives

 

 

 

 

 

 

 

 

 

 

 

 

Brijesh Kumar Srivastava, Atul Kumar,

I Dwivedy & Suprabhat Ray*

Epoxidation of 5-androsten-3b,17b-diol diacetate with MCPBA produces 5a,6a-epoxide at -20°C. Stereospecific opening of epoxide occurs on treatment with amines.

 

 

 

 

414

Synthesis of steroidal selenadiazoles

 

 

 

 

 

 

 

 

 

Shafiullah*, M Salman Hashmi & E H Khan

Synthesis of 3b-acetoxy-5a-cholest-6-eno[6,7-d] selena-diazoles 4-6 has been described.

 

 

 

 

 

 

 
416

A new route for the synthesis of bisunsaturated oxosulfones and bissulfones under
Friedel Craft’s conditions

 

 

 

 

 

 

 

 

 

D Bhaskar Reddy*, N Chandrasekhar Babu,

K Venugopal Reddy & V Padmavathi

A new class of 1-aroyl-2-styrylsulfonylethenes 4 and 1-arylsulfonyl-2-styrylsulfonylethenes 5 has been reported and a new route for 1,3,5-tribenzoylbenzene 6 is designed.

 

 

 

 

 

 

 

 
419

Synthesis of some new 3-(5-arylpyridin-2-yl)- and 8-(6-arylpyridin-2-yl)coumarins

 

 

 

 

 

 

 

 

 

 

 

 

D I Brahmbhatt* & Urvish R Pandya

3-(6-Arylpyridin-2-yl)coumarins 3a-f and 8-(6-aryl-pyridin-2-yl)coumarins 5a-f have been synthesised by the reaction of coumarinoyl methyl pyridinium salts 1 and 4 with Mannich bases 2a-f in the presence of ammonium acetate and acetic acid.

 

 

 

 

 

 

 

 
422

Synthesis of 2-(4-bromobenzoylamino)-5-aryloxymethyl-1,3,4-thiadiazoles

 

 

 

 

 

 

 

 

 

 

 

 

Xicun  Wang, Zheng Li*, Yuxia Da,

Jichou Chen & Xiuchun Wang

Reactions of 4-bromobenzoyl chloride with ammonium thiocyanate first, then with aryloxyacetic acid hydrazides under phase transfer catalysis give 1-aryloxyacetyl-4-(4-bromobenzoyl)thiosemicarbazides 3a-k. Compounds
3a-k on treatment with excess glacial acetic acid under reflux result in the formation of 2-(4-bromobenzoyl-amino)-5-aryloxymethyl-1,3,4-thiadiazoles 4a-k.

 

 

 

 

 

 

426

New cyanine dyes from 4,9-dioxopiperidino-[2,3-g]-1, 2, 3,4,6,7,8,9-octahy­dro-quinolino-quinone

 

 

 

 

 

H A Shindy*, A I M Koraiem,

A K Khalafallah & H A Soleiman

Arylidenes, heterylidenes and schiff bases derivatives derived from 4,9-dioxopiperidino[2,3-g]-1,2,3,4,6,7,8,9-octahydroquinolinoquinone have been oriented to prepare new photosensitizers, symmetrical bis(styryl, tetramethine, aza-styryl) cyanine dyes. The increase of photosensitization of the dyes is determined by studying their UV spectra.

 

 

 

 

 

 

 

 
430

Azlactones in heterocyclic synthesis: Part IV– A new route for the synthesis of 6-substituted and 6-arylidene-benzimidazo[1,2-c]quinazo-lines

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

N J Prameela Subhashini &

P Hanumanthu*

Condensation of 2-(o-aminophenyl)benzimidazole 1 with 4-arylidene-2-substituted oxazolin-5-ones 2 (azlactones) in acetic acid results in the formation of 5,6-dihydro-6-arylidenebenzimidazo[1,2-c]quinazolines 3 and 6-substituted benzimidazo[1,2-c]quinazolines 4. Structures of these compounds have been established based on their spectral data, and direct comparison with authentic samples prepared by unambiguous routes.

 

 

 

 

 

 

 

433

Polyethylene glycol mediated reductive decyanation of diphenylacetonitrile moderately enhanced by microwave heating

 

 

 

 

Pravin M Bendale,

Boudhayan Roy Chowdhury &

Bhushan M Khadilkar*

Rapid decyanation of alkyldiphenylacetonitriles with NaOH-PEG 400 in domestic microwave oven gives the corresponding hydrocarbon in excellent yield.

 

 

 

 

 

 

 

436

Wet alumina supported 3-carboxypyridinium chlorochromate selective oxidation of alcohols in solventless system

 

 

 

 

 

 

Majid M Heravi*, Reza Kiakoojory,

Maryam Mirza-Aghayan &

Mohammad Bolourtchian

A simple and selective method for the oxidation of alcohols to carbonyl compounds is described. It occurs on alumina supported CPCC under solvent-free conditions and is expedited by microwave irradiation.

 

 

 

 

 

 

438

Potentiometric measurements of para and nitro substituted aromatic acids in methanol

 

 

 

 

Cemal Ozeroglu* & Husnu Cankurtaran

A linear relationship has been found between pKa values of the para and nitro substituted aromatic acids in water and the half neutralization potential values measured by potentiometric titration of the same acids in methanol.

 

 

 

 

 

 

 

 
440

Synthesis of antiviral acyclic C-nucleosides incorporating thiazolo-1,3,4-oxa(thia)diazole or thiazolo-1,2,4-triazole structure as a nucleobase

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

L D S Yadav* & Smita Singh

Synthesis of the title nucleosides 5-7 via intramolecular chemoselective heterocyclization of 3-thioureidothiazo-lidinones 4 (R=d-glucopentyl or d-xylobutyl is reported.

 

 

 

 

 

 

 

 

 
443

Phytoconstituents of Artemisia vulcaris

 

 

 

 

 

 

 

 

 

 

 

 

 

S Ravi* & A J Lakshmanan

Two new compounds artemisia lactone 1 and vulcaris lactone 2 have been reported from the essential oil of Artemisia vulcaris (compositae).

 

 

 

 

 

 

 

Authors for correspondence are indicated by (*)

 

 

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