Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

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VOL. 45B

NUMBER 1

JANUARY 2006

CONTENTS

Rapid Communications

 

 

 

227

A new and simple synthetic approach to functionalized sulphone derivatives by the Suzuki-Miyaura cross-coupling reaction

 

IPC: Int.Cl.7 C 07 D

Synthesis of various highly functionalized sulphone derivatives are reported via the bis Suzuki-Miyaura (SM) cross-coupling reaction as a key step. In this regard, the dibromo sulphone prepared by the thermal rearrangement of corresponding sultine derivative has been used as a key building block to prepare various functionalized aromatic sulphone derivatives.

 

 

 

 

 

 

 

 

Sambasivarao Kotha* & Arun Kumar Ghosh

 

 

 

 

 

Papers

 

 

 

232

Synthesis of potent water soluble forskolin analo­gues

 

IPC: Int.Cl.7 C 07 C

Synthesis of potent water soluble forskolin derivatives having specificity towards positive inotropic activity is reported. The present study is based on our report of novel development using 2-hydroxyacyl analogues of forskolin.

 

 

 

 

 

Bansi Lal*, Ashok Kumar Gangopadhyay, Ramesh M Gidwani, Ramanujam Rajagopalan & Anil V Ghate

 

 

 

 

 

 

 

 

 

 

 

 

 

247

A simple synthesis of 5-spirobarbituric acids and transformations of spirocyclopropanobarbiturates to 5-substituted barbiturates

 

IPC: Int.Cl.7 C 07 D

A simple synthetic methodology for the synthesis of 5-spirobarbituric acids 2 and their transformations to 5-substituted barbituric acids 11 has been developed.

 

 

 

 

Palwinder Singh* & Kamaldeep Paul

 

 

 

 

 

 

 

252

Antioxidant and antimicrobial activity evaluation of polyhydroxycinnamic acid ester derivatives

 

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

Polyhydroxycinnamic acid esters 5a-p have been synthesized and their antioxidant, antimicrobial activity are studied. The SAR studies reveal that pyrogallol and catechol moieties are essential for good antioxidant activity. Butyl hydroxycinnamates exhibit higher antibacterial activity and none of them shows significant antifungal activity.

 

 

 

 

 

Somepalli Venkateswarlu, Marellapudi S Ramachandra,

Alluri V Krishnaraju, Golakoti Trimurtulu &

Gottumukkala V Subbaraju*

 

 

 

 

 

 

258

Chemoselective Knoevenagel reaction as a novel route for the synthesis of biscoumarinyl methyl­sulphones and 4+1, 1+4 approach synthesis of aminooxadiazolyl and N-(2,5-dimethyl)­pyrrolyl­coumarins

 

IPC: Int.Cl.7 C 07 D

 

 

 

 

 

 

Ganesh N Alawandi & Manohar V Kulkarni*

 

 

 

 

 

 

 

 

 

 

 

 

 

267

Novel approach for the rapid and efficient synthesis of heterocyclic Schiff bases and azetidinones under microwave irradiation

 

IPC: Int.Cl.7 C 07 D

2-Azetidinones 4 have been prepared by the reaction of Schiff bases 3 with chloroacetyl chloride and triethylamine. The reaction is carried out by conventional and microwave method.

 

 

 

 

Bhanvesh Naik & K R Desai*

 

 

 

 

 

 

 

272

Vitamin B12 and BF3-etherate as catalysts in synthesis of some C4-C12-alkyl b-D-xylo­pyr­ano­sides

 

IPC: Int.Cl.7 C 07 C

Synthesis of alkyl b-d-xylopyranosides 6 has been performed by vitamin B12-catalyzed reaction glycosylation of acetobromoxylose 1 with alkanols (ROH) 3 and with glycosylation of alcohols 3 with tetra-O-acetyl b-d-xylopyranose 7 in the presence of BF3-etherate, as a Lewis acid catalyst.

 

 

 

 

Zorica D Petrović*, Dejan Andjelković & Aleksandra Spasojević

 

 

 

 

 

 

 

276

Hard-soft acid-base (HSAB) principle and difference in d-orbital configurations of metals explain the regioselectivity of nucleophilic attack to a carbinol in Friedel-Crafts reaction catalyzed by Lewis and protonic acids

 

IPC: Int.Cl.7 C 07 C

 

 

 

 

Gautam Panda*, Jitendra K Mishra, Shagufta,

T C Dinadayalane, G Narahari Sastry &

Devendra S Negi

 

 

 

 

 

 

 

 

 

 

 

 

 

288

Condensation reactions of various nucleophiles with 3-formylchromone

 

IPC: Int.Cl.7 C 07 D

3-Formylchromones 1 have been condensed with 1-(2,4-difluorophenyl-2-[1,2,4]triazol-4-yl)ethanone in acetic anhydride to afford 3-[3-(2,4-difluorophenyl)-3-oxo-2-[1, 2, 4]triazol-4-yl)-propenyl]chromon-4-ones 2. 3-Formylchromones 1 when heated with benzo­[d]isoxazol-3-yl-acetic acid in dry pyridine yield the compounds 3-(2-benzo[d]isoxazol-3-yl-vinyl) chromon-4-ones 3. Further, 3-formylchromones 1 on heating with N-methylpiperizine in ethanol give 1-(2-hydroxy­phenyl)-3-(4-methylpiperazin-1-yl) propenones 4.

 

 

 

 

 

 

 

V B Halnor, N R Dalvi, N S Joshi, C H Gill &

B K Karale*

 

 

 

 

 

 

 

292

Pyrazolo-fused quinoline analogues: Synthesis of 1H-pyrazolo [3, 4-b] quinolines and 3-amino-1H-pyrazolo [3, 4-b] quinolines from 3-formyl and 3-cyano-2-chloroquinolines

 

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

Synthesis of 1H-pyrazolo [3,4-b] quinolines 6 is described in two steps from substituted 2-chloro-3-formyl quinolines 1.

 

 

 

 

 

 

 

Ambika Srivastava, Mrityunjay K Singh &

R M Singh*

 

 

 

 

 

 

 

 

 

 

 

 

 

297

Polymer-supported formate and zinc: A novel system for the transfer hydrogenation of aromatic nitro compounds

 

IPC: Int.Cl.7 C 07 D

A mild and efficient catalytic transfer hydrogenation (CTH) system has been developed for the facile reduction of aromatic nitro compounds using recyclable polymer-supported formate and commercial zinc dust.

 

 

 

 

 

 

G R Srinivasa, K Abiraj & D Channe Gowda*

 

 

 

 

 

Notes

 

 

 

302

Lithium chloride as an efficient catalyst for Friedlander synthesis of 1,8-naphthyridines via the use of microwave irradiation and pestle/mortar

 

IPC: Int.Cl.7 C 07 D

Microwave irradiation and pestle / mortar techniques have been employed successfully in the presence of lithium chloride for the synthesis of 1,8-naphthyridines 3 from 2-aminonicotinaldehyde 1 and active methylene compounds 2.

 

 

 

 

 

 

 

K Mogilaiah*, M Prashanthi & S Kavitha

 

 

 

 

 

 

 

305

Efficient deprotection of tetrahydropyranyl ethers by silica sulfuric acid

 

IPC: Int.Cl.7 C 07 D

 

 

 

 

 

 

 

Abdol R Hajipour*, Amin Zarei, Leila Khazdooz,

Seied A Pourmousavi, Saeed Zahmatkesh & Arnold E Ruoho

 

 

 

 

 

 

 

 

 

 

 

 

309

Synthesis and antimicrobial screening of 3H,11H-9-methyl-3-oxopyrano[2,3-f]cinnolino[3,4-c]pyrrazole and its derivatives

 

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

Various 3H,11H-9-methyl-3-oxopyrano[2,3-f]cinno­lino[3,4-c]pyrrazole 4, 3H-9-methyl-3-oxo-11-(N-me­thylene­morpholino)pyrano[2,3-f]cinnolino[3,4-c]py­rra­­zole 5, 3H-9-methyl-3-oxo-11-phenyl pyrano[2,3-f]cinnolino[3,4-c]pyrrazole 6 and 3H-9-methyl-3-oxo-11-(4-methyl-7-methoxy-2-oxo-2H-[1]-benzopy­ran-6-yl)­pyrano[2,3-f]cinnolino[3,4-c]pyrrazole 7 have been synthesized from 6-aminocoumarins and screened for their antimicrobial activities and are found to possess significant antibacterial and anti­fungal activities.

 

 

 

 

Bharati P Choudhari & Vinata V Mulwad*

 

 

 

 

 

 

 

314

Synthesis and antimicrobial screening of 5H,7H-N-(coumarin-6-yl)-2,8-diphenyl-5,7-dioxo-4,5,6,7-tetrahydrobenzimidazo[5,6-c]furan and 5H,7H-N-(coumarin-6-yl)-2, 8-diphenyl-5, 7-dioxo-6-(7-me­thoxy-4-methylcoumarin-6-yl)-4, 5, 6,7-tetrahydro benzimidazo[5,6-c]pyrrole

 

IPC: Int.Cl.7 C 07 D

Synthesis and antimicrobial screening of 5H,7H-N-(coumarin-6-yl)-2,8-diphenyl-5,7-dioxo-4,5,6,7-tetra­hydrobenzimidazo[5,6-c]furan 5 and 5H,7H-N-(cou­marin-6-yl)-2,8-diphenyl-5,7-dioxo-6-(7-methoxy-4-methylcoumarin-6-yl)-4,5,6,7-tetrahydro benzi­mi­dazo­[5,6-c]pyrrole 6 via Schiff base formation of 6-amino­coumarin has been described.

 

 

 

 

 

 

B P Choudhari & V V Mulwad*

 

 

 

 

 

 

 

 

 

 

 

 

 

318

Synthesis of novel bone-targeted agents for treatment of osteoporosis

 

IPC: Int.Cl.7 C 07 D

Design, synthesis and biological activities of novel bone-targeted raloxifene-bisphosphonate conjugates are reported.

 

 

 

 

 

 

Junbo Wang, Chunhao Yang, Huasheng Ding,
Xueming Yan, Xihan Wu & Yuyuan Xie*

 

 

 

 

 

 

 

322

A simple method for deprotection of tert-butyldimethylsilyl ethers by using stannous chloride under microwave irradiation

 

IPC: Int.Cl.7 C 07 C

A facile regeneration of hydroxy compounds from their tert-butyldimethylsilyl ethers in presence of stannous chloride under solvent free conditions using domestic microwave oven has been performed efficiently.

 

 

 

 

 

 

Vinod H Jadhav, Hanumant B Borate & Radhika D Wakharkar *

 

 

 

 

 

 

 

325

Electrophilic substitution reactions on 3-bro­mo­acetylcoumarins

 

IPC: Int.Cl.7 C 07 D

Attempted nitration and bromination of 3-bromoacetylcoumarins result in the formation of racemic 3-w-bromonitroacetylcoumarins and 3-w-dibromoacetylcoumarins.

 

 

 

 

 

K Y Anklekar, R A Kusanur & M V Kulkarni*

 

 

 

 

 

 

 

 

 

 

 

 

 

328

Convenient synthesis of (E)-methyl O-alkyl­ferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza

 

IPC: Int.Cl.7 C 07 C

A convenient two step synthesis of (E)-methyl O-alkylferulate described from vanillin. Reaction of vanillin with allyl-, prenyl- or geranyl- bromide has afforded respective alkyl ethers which on reaction with phosphorane, under microwave irradiation, gives (E)-methyl O-alkylferulates in high yield. In an alternative approach vanillin on reaction with phosphorane provides (E)-methyl ferulate which on reaction with the corresponding bromides gives (E)-methyl O-alkylferulates.

 

 

Rajesh P Mahajan, Shamkant L Patil* &

Raghao S Mali *

 

 

 

 

 

 

 

332

Pinacol coupling of carbonyl compounds by using Al-NaOH/MeOH under microwave irradiation

 

IPC: Int.Cl.7 C 07 C

Microwave irradiation accelerates the Pinacol coupling reaction of aromatic aldehydes and ketones  with Al in aqueous NaOH-MeOH in high yield  within 5- 15 min.

 

 

 

 

Mohsen Mazaheri Tehrani* & Jila Asghari

 

 

 

 

 

 

 

335

Synthesis of 4-aryl-5-oxo-1H,4H-5,6,7,8-tetra­hydro­­­quinoline and 4-aryl-5-oxo-1H-4,5,6,7-tetra­hydro­cyclopenteno[b]pyridine derivatives by ultra­­sound irradiation and by conventional methods

 

IPC: Int.Cl.7 C 07 D

Arylhexahydro-quinoline-3-carboxylates 4a-d and arylcyclopenteno[b]pyridine-3-carboxylates 6a-e have been synthesized by the condensation of cyclic 1,3-diones with aromatic aldehydes and b-aminocrotonate using thermal and ultrasound irradiation methods.

 

 

 

 

D Thirumalai, P Murugan & V T Ramakrishnan*

 

 

 

 

Authors for correspondence are indicated by (*)

IPC: International Patent Classification

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