Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

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VOL. 45B

NUMBER 2

FEBRUARY 2006

CONTENTS

Rapid Communications

 

 

 

429

Cerium catalysed Michael addition to a,b-unsaturated oximes: A facile and efficient synthesis of substituted pyridines

 

IPC: Int.Cl.7 C 07 D

CeCl3.7H2O-NaI is found to be an effective catalyst for the synthesis of various tetra-substituted pyridine derivatives via Michael addition of b-dicarbonyl compounds to a,b–unsaturated oximes and subsequent ring closure by cyclo-dehydration of these products.

 

 

 

 

 

Sanjay Kumar, Anil Saini & Jagir S Sandhu*

 

 

 

 

Advances in Contemporary Research

 

 

 

433

Marine algal natural products: Contributions from India in the global context

 

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

The review describes Indian contribution in the field of marine natural products in the global context. Several terpenes (mostly sesqui and diterpenes), steroids, ceramides, nitrogen pigments, heterocycles, aromatic compounds and polyethers have been reported from Indian marine algae.

 

 

 

 

Nittala S Sarma*, M Sri Rama Krishna & Sk G Pasha

 

 

 

 

Papers

 

 

 

450

Propionic acids in organic synthesis: Novel synthesis of benzimidazole, 3,1-benzoxazine, 3-aminoquinazoline and 3-aminothieno[2,3-d]pyrimidine derivatives containing 2-naphthyl propionyl moiety

 

IPC: Int.Cl.7 C 07 D

Naproxenoyl chloride 2 is reacted with some nucleophilic reagents as ammonium thiocyanate and sodium azide to produce the novel isothiocyanate 3 and azide 4 derivatives, respectively. The novel quinazolinone 11 was synthesized by acylation of methyl anthranilate with acid chloride 2 followed by treatment with hydrazine hydrate.

 

 

 

 

Abdullah G M Al-Sehemi*, A M Sh El-sharief &

Y A Ammar

 

 

 

 

 

 

 

 

 

 

456

Iodine (III) mediated synthesis of new 5-aryl-3-(4-hydroxy-6-methyl-2H-pyran-2-oxo-3-yl)-1-phenyl­pyra­zoles from dehydrogenation of 5-aryl-3-(4-hydroxy-6-methyl-2H-pyran-2-oxo-3-yl)-1-phenylpyrazolines

 

IPC: Int.Cl.7 C 07 D

 

 

 

Om Prakash*, Ajay Kumar, Mayank Kinger &

Shiv P Singh

 

 

 

 

 

 

 

461

A convenient stereoselective synthesis of β-d-gluco­pyra­nosides

 

IPC: Int.Cl.7 C 07 H 3/00

A simple, stereoselective synthesis of β-d-glucopyranosides via glycosidic bond has been reported.

 

 

Vishal Y Joshi & Manohar R Sawant*

 

 

 

 

 

 

 

466

Solvent-free improved syntheses of some substituted 1, 3-diaryl-propenones and 3,5-diaryl-6-carbethoxy­cyclo­hexenones under microwave irradiation and their antibacterial activity

 

IPC: Int.Cl.7 C 07 C

Substituted 1,3-diarylpropenones 3 and their trans­formation products 3,5-diaryl-6-carbethoxy­cyclo­hexenones 4 have been synthesized in improved yield using solvent-free solid phase microwave irradiation as compared to the conventional method and antibacterial activity of these have been evaluated.

 

 

Yajuvendra S Jhala, Shiv S Dulawat & B L Verma*

 

 

 

 

 

 

 

 

 

 

470

The reaction of aromatic aldehydes and 5,5-dimethyl-1,3-cyclohexanedione under solvent-free grinding conditions

 

IPC: Int.Cl.7 C 07 D

The reaction of aromatic aldehyde and 5,5-dimethyl-1,3-cyclohexanedione under grinding conditions has been catalyzed by KF/Al2O3 or silica sulfate and obtained two products:2,2-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1, 8-dioxooctahydro- xanthene and their derivatives. In addition, the 2-amino-4-aryl-3-cyano-7,7- dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran can be obtained in this condition.

 

 

Tong-Shou Jin*, Ai-Qing Wang, Hui Ma,

Jian-She Zhang & Tong-Shuang Li

 

 

 

 

 

 

 

475

Quantitative structure activity relationship studies of diarylimidazoles as selective COX-2 inhibitors

 

IPC: Int.Cl.7 C 07 D

QSAR analysis has been performed on a series of diarylimidazole derivatives in order to gain further structural insights for developing newer COX-2 inhibitors.

 

 

M R Yadav*, D S Puntambekar, K P Sarathy,

S Vengurlekar & R Giridhar

 

 

 

 

 

 

 

483

Use of polyfunctionalized ethylene synthons: Convenient synthesis of biologically active tri­fluoro­methyl containing N-substituted-benzoyl­pyrazoles and triazole

 

IPC: Int.Cl.7 C 07 D

Several ethylene synthons have been used in the building of fluorine containing pyraazoles and their bioactivity is also reported.

 

 

Li Ming*, Wen Lirong, Wang Xiao, Yao Changsheng, Fu Weijun, Zhao Guilong,

Hu Fangzhong & Yang Huazheng

 

 

 

 

 

 

 

 

 

 

 

 

489

Synthesis and antiviral activities of N-substituted-2-substituted-benzimidazole derivatives

 

IPC: Int.Cl.7 C 07 D

 

 

 

Ashish Kumar Tewari* & Anil Mishra

 

 

 

 

Notes

 

 

 

494

Synthesis and antimicrobial evaluation of some 4- or 6-chloroisatin derivatives

 

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

Several semicarbazones and hydrazones of isomeric chloroisatins have been prepared and their in vitro antimicrobial properties against bacteria and fungi are reported.

 

 

S N Pandeya, A S Raja* & G Nath

 

 

 

 

 

 

 

500

Microwave thermolysis-Part IX: A selective and rapid oxidation of benzylic alcohols using clay supported ammonium nitrate

 

IPC: Int.Cl.7 C 07 C

 

 

 

H M Meshram*,B Muralidhar, B Eeshwaraiah,
K Ramesh Babu, D Aravind & J S Yadav

 

 

 

 

 

 

 

503

An efficient and chemoselective method for conversion of carbonyl compounds to 1,3-oxathiolanes with 2-mercaptoethanol catalyzed by TiCl4-montmorillonite

 

IPC: Int.Cl.7 C 07 D

Formation of 1,3-oxathiolanes from aldehydes and ketones using 2-mercaptoethanol in the presence of TiCl4-montmorillonite under mild reaction conditions in excellent yield is described. Chemoselective monothioacetalization of aldehyde in the presence of ketone can also be achieved in high yield.

 

 

 

 

Tong-Shou Jin*, Rui-Qiao Zhao, Yan-Ran Ma,

Mi-Na Yang, Jun-Jie Guo & Tong-Shuang Li

 

 

 

 

 

 

 

 

 

 

 

 

 

506

NMR and X-ray characterization of the diastereomeric pinacols derived from the photo-irradiation of o-alkoxy­acetophenones

 

IPC: Int.Cl.7 C 07 D

A simple 1H NMR characterization of diastereomeric pinacols derived from o-alkoxy-acetophenones is described. The 1H NMR spectral assignments are based on molecular modeling and substantiated by X-ray crystallographic structural assignment of a diastereomer.

 

 

 

 

 

Rajinder Singh, P K Garg, M S Hundal & M P S Ishar*

 

 

 

 

 

 

 

510

Reduction of aromatic nitro compounds using microwave heating assisted with alumina-supported hydrazine / Fe(NO3)3·9H2O

 

IPC: Int.Cl.7 C 07 C

Aromatic nitro compounds are easily reduced to the corresponding amino compounds using microwave heating assisted with hydrazine hydrate supported on alumina in the presence of Fe(NO3)3.·9H2O.

 

 

 

 

Chang-Rui Zhang & Yu-Lu Wang*

 

 

 

 

 

 

 

512

A facile synthesis and characterization of 2-(3˘,4˘-dihydrocarbazol-1˘-yl)-2,3,4,5-tetrahydroindolo­[2,3-b]azepanes

 

IPC: Int.Cl.7 C 07 D

Synthesis of 2-(3˘,4˘-dihydrocarbazol-1˘-yl)-2,3,4,5-tetra­hydro­­indolo[2,3-b]azepanes 2 by the reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles 1 in the presence of hydroxylamine hydrochloride and formic acid.

 

 

I Antony Danish & K J Rajendra Prasad*

 

 

 

 

 

 

 

 

 

 

 

 

 

517

Synthesis of pyrazolines, isoxazolines and amino­pyri­midines as biological potent agents

 

IPC: Int.Cl.7 C 07 D

Chalcones, 2-phenylamino-4-(4'-fluorophenylamino)-6-[4'-{3''-(phenyl/substituted phenyl /2'''-furanyl/3'''-pyridinyl)-2''-propenon-1''-yl} phenylamino]-s-triazines 6a-j have been prepared from ketone 5 based on s-triazine nucleus. These chalcones 6a-j on cyclisation with hydrazine hydrate, hydroxylamine hydrochloride and guanidine nitrate give the corresponding pyrazolines 7a-j, isoxazolines 8a-j and aminopyrimidines 9a-j, respectively. Antimicrobial activities of all synthesized compounds have been performed by using cup-plate method against bacteria and by using poisoned food technique against fungi.

 

 

 

 


 

\

 

 

Anjani Solankee* & Indrajit Thakor

 

 

 

 

 

 

 

523

Synthesis of new 1, 10-diethoxy-1H-pyrano[4, 3-b]quino­lines and their antibacterial studies

 

IPC: Int.Cl.7 C 07 D

 

 

 

 

 

 

a) R1=R2=R3=R4=H

b) R1=CH3, R2=R3=R4=H

c) R1=R2=R4=H, R3=OCH3

d) R1=R2=R4=H, R3=Cl

e) R2=R3=H, R1=R4=CH3

 

 

 

 

T Dhanabal, T Suresh & P S Mohan*

 

 

 

 

 

 

 

 

 

 

 

 

 

526

Synthesis of 5-arylidene-2-aryl-3-(benzotriazolo­aceta­midyl)-1,3-thiazolidin-4-ones as analegesic and anti­microbial agents

 

IPC: Int.Cl.7 C 07 D

Benzotriazole on reaction with ethyl chloroacetate affords 1, which on treatment with NH2NH2.H2O yields 2. Condensation of N1 (acetohydrazido) benzotriazole 2 with various carbonyls gives arylidene acetohydrazido benzotriazoles 3 which on cycloaddition with mercapto acetic acid yields the corresponding 4-thiazolidinones 4. Treatment of these 4-thiazolidinones with various carbonyl compounds afford 5-arylidene-2-aryl-3-benzotriazoloacetamidyl-1,3-thiazolidin-4-ones 5

 

 

 

 

K C Asati, S K Srivastava* & S D Srivastava

 

 

 

 

 

 

 

532

Synthesis and characterization of a new chromano­isoxazole

 

IPC: Int.Cl.7 C 07 D

 

 

 

 

 

Y L N Murthy*, Rani Nanda, K Ravi Kumar &

G Y S K Swamy

 

 

 

 

 

 

 

535

Synthesis of 2-(2-phenylethyl)chromones

 

IPC: Int.Cl.7 C 07 D

2-(2-Phenylethyl)chromones have been obtained by selective reduction of double bond of the styryl group in 2-styrylchromones involving catalytic hydrogen transfer reaction using ammonium formate in the presence of Pd-C.

 

 

 

 

Sharda Goel, Shashi & J K Makrandi*

 

 

 

 

 

 

 

 

 

 

 

 

 

537

Microwave assisted convenient and facile regeneration of carbonyl compounds from semicarbazones, phenyl­hydrazones and tosylhydrazones using phosphoric acid in solvent-free conditions

 

IPC: Int.Cl.7 C 07 D

Phosphoric acid is an efficient and mild reagent for regeneration of aldehydes from semicarbazones, phenylhydrazones and tosylhydrazones. The reactions have been carried out in solvent-free condition under microwave irradiation.

 

 

 

 

Krishna Banerjee, Alok Kumar Mitra &

Amarendra Patra*

 

 

 

 

 

 

 

540

Attempted synthesis of substituted carbazoles from 1-oxo-1,2,3,4-tetrahydro-carbazoles and 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles

 

IPC: Int.Cl.7 C 07 D

Synthesis of annelated carbazoles 2 and 4 by the reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles 1 and 1-hydroxyimino-1,2,3,4-tetrahydrocarbazoles 3 with vinyl acetate has been reported.

 

 

 

 

 

 

I Antony Danish & K J Rajendra Prasad*

 

 

 

 

 

 

 

546

A rapid microwave assisted synthesis of N, N'-diarylureas under solvent-free condition

 

IPC: Int.Cl.7 C 07 C

A novel microwave assisted phosgene-free synthesis of N,N˘-diaryl ureas under solvent free conditions has been described.

 

 

 

1a                            2                                                              3a

 

 

 

S Sarveswari & T K Raja*

 

 

 

 

 

 

 

 

 

 

 

 

 

548

Cytotoxic ent-kaurane diterpenoids from Isodon  racemosa (Hemsl) Hara

 

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

A new ent-kaurane diterpenoid racemosin A (1) and three known compounds, leukamenin E (2), glaucocalyxin A (3) and wangzaozin A (4), have been isolated from the leaves of Isodon racemosa (Hemsl) Hara. Compounds 14 show significant cytotoxic activity against Bel-7402 and HO-8910 cells.

 

 

 

 

 

1

 

 

 

 

Lan Ding*, Guo-An Liu, Lai Wang, Kun Sun &

Han Wang

 

 

 

 

 

 

 

552

Synthesis of hexahydro-1,3,5-triazines: A new approach from N-substituted-a-aminoisothiocyanates

 

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

Azomethines 1a-m react with ammonium thiocyanate/acetic acid to give the corresponding N-substituted-a-amino­isothiocyanates 2a-m which are found to be excellent starting materials for the synthesis of hexahydro-1,3,5-triazines 3a-m. Compounds 2a-m on treatment with toluene-2,4-diisocyanate give the corresponding hexahydro-1,3,5-triazines 3a-m in good yields.

 

 

 

 

 

 

Harish Kumar*, Rita Goyal, Anupama Parmar & Sukhwinder Kaur

 

 

 

 

 

 

 

 

 

 

 

 

 

558

Synthesis of 2-phenylimino-3-aryl-4-S-benzyl-6-hepta-O-acetyl-b-lactosylimino-2,3-dihydro-1,3,5-thiadiazine hydrochlorides

 

IPC: Int.Cl.7 C 07 D

2-Phenylimino-3-aryl-4-S-benzyl-6-hepta-O-acetyl-b-lactosylimino-2,3-dihydro-1,3,5-thiadiazine hydrochlorides 3 are prepared by the interaction of 1 with 2

 

R =

a: H

d: p-tolyl

g: p-Cl-phenyl

 

b: o-tolyl

e: o-Cl-phenyl

 

 

c: m-tolyl

f: m-Cl-phenyl

 

 

P V Tale & S P Deshmukh*

 

 

 

 

 

 

 

561

Selective oxidation of secondary over primary hydroxyl group

 

IPC: Int.Cl.7 C 07 C

Selective oxidation of oligoethylene glycol ether methyl 12(13)–hydroxy-13(12)-[11-hydroxy-3,6,9-trioxa-undecyl-1-oxy]-octadec-9-enoate 3 has been studied using pyridinium chlorochromate (PCC). The reaction has resulted in the formation of methyl 12(13)–oxo-13(12)-[11-hydroxy-3,6,9-trioxa-undecyl-1-oxy]-octadec-9-enoate 5 as an unexpected product wherein only the secondary hydroxyl group has been oxidized while the primary hydroxyl group has remained intact.

 

 

 

Sukhprit Singh* & Vandana Mahajan

 

 

 

 

 

 

 

 

 

 

564

Trimethylammonium fluorochromate (TriMAFC): A convenient new and mild reagent for oxidation of organic substrates

 

IPC: Int.Cl.7 C 07 C

 

 

 

 

 

S A Seyed Sadjadia & S Ghammamy*b

 

 

 

 

 

 

 

568

Synthesis of pyrazolines promoted by Amberlyst-15 catalyst

 

IPC: Int.Cl.7 C 07 D

The synthesis of substituted pyrazolines in good yield by the cyclization of propenones using Amberlyst–15 catalyst is described. The method affords a cheap, nontoxic and ecofriendly means of synthesizing pyrazoline derivatives. The method also enables the recovery of the catalyst and the solvent used without any difficulty.

 

 

B Shivarama Holla*, M Mahalinga, Boja Poojary, Mithun Ashok & P M Akberali

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

Int. Cl7.: International Classification, 7th Edition, 1999