Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

Total visitors:2,848 since 31-03-07

VOL. 46B

NUMBER 4

APRIL 2007

CONTENTS

Papers

 

 

 

643

One-pot Reformatsky-Imine addition reaction leading to the synthesis of structurally diverse
b-lactams

 

IPC: Int.Cl.8 C07D

b-Lactams are well-known for being the part of various antibiotics. The Reformatsky-imine addition reaction of a-bromoethylacetate with aldimines derived from 3,4-methylenedioxy benzaldehyde and a-methylcinnamaldehyde provided an efficient and practical access to structurally diverse b-lactams. All the new b-lactams have been identified as 1,4-diaryl-2-azetidinones through their detailed spectral studies. Further, it also reveals that the styryl bond of a-methylcinnamylideneanilines did not participate in the reaction and gives b-lactams contrary to their analogues cinnamylideneanilines and o-nitro­cinn­amylidene anilines which gave d-lactams.

 

 

Jaspreet Rajput*, Baldev Singh & Kewal Krishan Singal

 

 

 

 

 

 

 

649

A facile and high efficient synthesis of nitriles from aldoximes and primary amides with a mixture of triphenylphosphine/2, 3-dichloro-5, 6-dicyanobenzoquinone (PPh3/DDQ) under neutral conditions

 

IPC: Int.Cl.8 C07C

Aldoximes are immediately converted to their corres­ponding nitriles with a mixture of triphenylphosphine and 2,3-dichloro-5,6-dicyanobenzoquinone in di­chloro­methane under neutral conditions at room temperature. Also, nitriles are formed from the reaction of primary amides with this reagent in refluxing acetonitrile under neutral conditions.

 

 

Ghasem Aghapour* & Marjan Amirabadi

 

 

 

 

 

 

 

 

 

 

 

 

 

653

Synthesis of some new 4-thiazolidinones and thiazin-4-ones as biologically potent agents

 

IPC: Int.Cl.8 C07D

Some new 4-thiazolidinones 6-(2-aryl-4-thia­zolidino­nes)-2,5-bis-(4-methoxy-phenyl)-3-pyridazinones 5a-e, 6-(2-aryl-5-methyl-4-thiazolidinones)-2,5-bis-(4-meth-oxyphenyl)-3-pyridazinones 6a-e and thazin-4-ones 6-(2-aryl-1,3-thiazin-4-ones)-2,5-bis-(4-methoxy­phenyl)-3-pyridazinones 7a-e are synthe­sised and evaluated for antibacterial and antifungal activity.

 

 

 

 

 

 

 

 

 

 

 

J N Gadre*, Smita Nair & Saurabh Chitre

 

 

 

 

 

 

 

660

A new and efficient method for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione under sol­vent and catalyst free conditions

 

IPC: Int.Cl.8 C07D

A new and efficient method has been used for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione without any catalyst and solvent under microwave irradiation. A number of condensation products are prepared in a very short reaction time with high yields.

 

 

 

 

 

 

 

 

 

 

Ch Sanjeeva Reddy*, A Nagaraj & P Jalapathi

 

 

 

 

 

 

 

 

 

 

 

 

 

664

On the reaction of anthranilic acid with thionyl chloride : Iminoketene intermediate formation

 

IPC: Int.Cl.8 C07D

2-(Sulfinylamino) benzoyl chloride is formed on treating anthranilic acid with thionyl chloride. The formation of iminoketene intermediate from 2-(sulfinylamino) benzoyl chloride explains many of its reactions.

 

 

 

 

 

 

 

 

 

 

 

Dominic E Jacob* & Lopez Mathew

 

 

 

 

 

 

 

669

Efficient synthesis of bis(indolyl) methanes in aqueous medium catalyzed by molybdenyl acetylacetonate

 

IPC: Int.Cl.8 C07D

A mild and efficient electrophilic substitution reaction of indoles with aldehydes and ketones has been carried out in water using a catalytic amount of MoO2(acac)2 to afford the corresponding bis(indolyl)methanes in excellent yields. Vibrindole A, a bacterial metabolite and 3,3'-diindolyl methane, a potent anti-carcinogenic agent has also been successfully synthesized in excellent yield using this methodology.

 

 

 

 

 

 

 

 

 

 

 

B Banerjee, S K Mandal & S C Roy*

 

 

 

 

 

 

 

 

 

 

 

 

 

674

The novel N,S-substituted nitro dienes from the reactions of some mono(alkylthio)-substituted
2-nitrodienes with piperazine and thiomorpholine and a structural study

 

IPC: Int.Cl.8 C07D

Thiosubstituted nitrodien compounds 1a-f are obtained from 2-nitropentachlorobutadiene and some alifatic thiols. Compounds 1a-f have reacted with thiomorpholine 2 and yielded 3a-f in CH2Cl2. The compounds 5a-f have been obtained by the reactions of 1a-f with N-(diphenylmethyl)piperazine 4 in CH2Cl2. 2-Nitro-3,4,4-trichloro-1-(ethylthio)-1-[4-(1-diphenylmethyl)-piperazin-1-yl]-1,3-butadiene 5a is synthesized and its crystal structure is determined. The compound 5a crystallizes in the Orthorhombic crystal system (space group P212121) with the unit cell parameters a = 9.4240(2) Ĺ, b = 14.4007(2) Ĺ, c = 18.1891(2) Ĺ, a, b, g = 90°, V = 2468.48(7) Ĺ3, Z = 4. The structure has been solved by direct methods (SIR92) and refined to the residual index R1 = 0.078.

 

 

 

 

 

 

 

Cemil Ibis* & N Gulsah Deniz

 

 

 

 

 

 

 

681

Synthesis and spectral studies of some heteroarylpiperidin-4-ones and their derivatives

 

IPC: Int.Cl.8 C07D

The 1H and 13C NMR spectra have been recorded for t(3)-methyl-r(2), c(6)-di-2˘-furylpiperidin-4-one 1, t(3)-ethyl-r(2), c(6)-di-2˘-furylpiperidin-4-one 2, t(3)-isopropyl-r(2), c(6)-di-2˘-furylpiperidin-4-one 3, t(3), t(5)-dimethyl-r(2), c(6)-di-2˘-furylpiperidin-4-one 4 and their derivatives
5-12 and analysed.

 

 

 

 

 

 

A Manimekalai*, J Jayabharathi, V M Porselvi & N Prabha

 

 

 

 

 

 

 

 

 

Notes

 

 

 

690

Synthesis and antimicrobial activity of novel linearly fused 5-substituted- 7-acetyl-2,6-dimethyl­oxazolo[4,5-f]indoles

 

IPC: Int.Cl.8 C07D

 

 

 

Dundappa S Donawade, A V Raghu &

Guru S Gadaginamath*

 

 

 

 

 

 

 

694

Remote dianions and their application in the synthesis of macroheterocycles

 

IPC: Int.Cl.8 C07D

A useful sequence of reactions in one-pot. for the syntheses of nitrogen, oxygen and phosphorus macroheterocycles is described. The key step involves the generation of dianion that attacks to a variety of dielectrophiles leading to compounds 3-9 in good yields.

 

 

M S Singh*, Pratibha Singh, M David Raju &

A K Singh

 

 

 

 

 

 

 

 

 

 

 

 

 

698

Synthesis and evaluation of some 1,4-dihydro­pyridine and their derivatives as antihypertensive agents

 

IPC: Int.Cl.8 C07D

 

 

 

Shashikant R Pattan*, V P Rasal,

N V Venkatramana, A B Khade, S R Butle,

S G Jadhav, B G Desai, F V Manvi

 

 

 

 

 

 

 

702

Pyrido[2,3-d]pyrimidines and their ribofurano­sides: Synthesis and antimicrobial investigations

 

IPC: Int.Cl.8 C07D

4-Amino-5,7-disubstituted pyrido[2,3-d]pyrimidines 4-amino-5,7-disubstituted pyrido[2,3-d]pyrimidine-2(1H)-thiones and 4-amino-3,5,7-trisubstituted pyrido [2,3-d] pyrimidines-2,4-(1H,3H)-dione and their ribofuranosides have been synthesized. The antimicrobial activities of all these derivatives have been studied.

 

 

Naresh Kumar, Sangeeta Tiwari & Ashok K Yadav*

 

 

 

 

 

 

 

 

 

 

 

 

707

Ce(IV) ammonium nitrate catalyzed chemo­selective deprotection of acetonides

 

IPC: Int.Cl.8 C07C

Highly chemoselective deprotection of diacetone sugars have been achieved at room temperature in excellent yields using commercially available ceric ammonium nitrate (20 mole%) in moist CH3CN.

 

 

 

S Jana & S C Roy*

 

 

 

 

710

Cascade synthesis of racemic 3-arylphthalides

 

IPC: Int.Cl.8 C07C

 

 

 

S T Patil & A V Karnik*

 

 

 

 

 

 

 

713

Ecofriendly solvent free microwave enhanced alkyl migration in N-alkyl anilines in dry media conditions

 

IPC: Int.Cl.8 C07 C

A rapid and efficient microwave enhanced synthesis of para alkyl anilines on dry media is reported.

 

 R1- Alkyl

 R2- Alkyl / Br

 R3- Alkyl / NH2 / Cl

 

 

S Selvakumar, M Easwaramurthy & G J Raju*

 

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

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