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Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

 

 

 

VOLUME 43 B

NUMBER 12

DECEMBER  2004

 

 

CONTENTS

 

 

 Papers

 

1
OC

185

Synthesis and characterization of {[(n-Bu)2 Sn(O2CCH=CHAr)]2O}2 and crystal struc­ture of {[(n-Bu)2Sn(O2CCH=CHPh)]2O}2

 

IPC: Int.Cl.7 C 07 C 133/20

Ten organotin compounds {[(n-Bu)2Sn (O2CCH = CHAr)]2O}2 have been synthesized by the reaction of (n-Bu)2SnO with ArCH=CHCO2H in 1:1 molar ratio. The crystal structure of {[(n-Bu)2 Sn(O2CCH = CHPh)]2O}2 is determined by X-ray single crystal diffraction.

 

 

 

 

Handong Yin*, Chuanhua Wang & Chunlin Ma

 

2
OC

337

Synthesis of some novel spiro heterocycles

 

IPC: Int.Cl.7 C 07 D 239/00

 

A new class of spiro pyrimidinetriones, thioxo­pyri­midinediones, pyrazolidi-nediones  and isoxazoli­ne­-d­iones are prepared from dihydropyridine/ pyran/thio­pyran dicarboxylates.

 

 

 

V Padmavathi*, B Jagan Mohan Reddy, A Padmaja, K Venugopal Reddy & M Rajagopala Sarma

 

3
OC

217

Synthesis and mesomorphic behaviour of 3-[4-alkyloxyphenyl]-5-[3, 4-ethylenedioxybenzyl]-2-isoxazolines

 

IPC: Int.Cl.7 C 07

A simple homologous series of 3-[4-alkyloxyphenyl]-5-[3,4-methylenedioxybenzyl]-2-isoxazolines having chiral sources have been synthesized by the reaction of aldoximes with safrole using chloramine-T. The synthesized compounds exhibit chiral nematic phase (N*), smectic A (SA) and chiral smectic phases (SC*).

 

 

K B Umesha, K M L Rai*, Nagappa &

J Mahadeva

4
OC

339

 

Efficient synthesis of 1,2,4-triazolo[4,3-a][1,8]­naphthyridines using nitrous acid under micro­wave irradiation

 

IPC: Int.Cl.7 C 07

 

A simple and efficient protocol for the synthesis of 1,2,4-triazolo[4,3-a][1,8]naphthyridines using nitrous acid under microwave irradiation is described.

 

 

K Mogilaiah*, M Prashanthi & K Vidya\

5
OC

089

 

Microwave induced synthesis of 3/4-substituted- 2-thioxo-/2-oxo-6-thioxo-1,2,3,4,6,7 hexahydro­thi­a­ zolo [4, 5-d] pyrimidine and thiazole derivatives

IPC: Int.Cl.7 C 07 D 239/00, 277/00

 

3/4-Substituted-2-oxo-6-thioxo-1,2,3,4,6,7 hexa­ hydro­thi­a­zolo[4,5-d] pyrimidine derivatives 3, 3/4-substituted-2, 6-dithioxo-1, 2, 3, 4,6,7-hexahydro­thia­zol­o­[4,5-d]pyrimidine 4 and 4,5-substituted thiazole derivatives 6 have been synthesized by using MW irradiation technique, which gives better yield than the conventional method.

 

 

Vijay V Dabholkar* & Syed Sagir Ahmed

6
OC

261

 

Microwave accelerated Pechmann synthesis of new isoxazolyl coumarins in dry media

IPC: Int.Cl.7 C 07 D 311/00

 

A fast and efficient synthesis of isoxazolyl coumarins 2 has been performed via the Pechmann reaction by microwave irradiation on solid support, montmorillonite K-10, which also acts as lewis acid catalyst. New isoxazolyl coumarins have been prepared for the first time under dry conditions using microwave and by conventional method.

 

 

E Rajanarendar*, P Ramesh & K Ramu

7
OC

275

 

Synthesis, characterization and electrochemical behaviour of some substituted 2-phenyl-4-(4˘-arylazophenyl)-3-thioxo-2H,3,4-dihydro-2,4,9,10-tetra­azaphenanthren-1-ones

 

IPC: Int.Cl.7 C 07 D 221/10

The electrochemical reduction of some substituted 2-phenyl-4-(4˘-arylazophenyl)-3-thioxo 2H-3, 4˘-di­hydro-2, 4, 9, 10-tetraazaphenan threne-1-ones has been studied over wide pH range.The kinetic parameters have also been studied.

 

 R = (a) H, (b) 4˘-Cl, (c) 4˘-OH, (d) 3˘- C2H5

 

 

Pratibha Sharma*, Ashok Kumar, Manisha Sharma & Siya Upadhyay

 

8
OC

396

 

Porcine pancreas lipase catalysed acetylation of b-cyclodextrin anchored 4-t-butylcyclohexanol

 

IPC: Int.Cl.7 C 07 C 13/18

Porcine pancreas lipase catalyzed acetylation of 4-t-butylcyclohexanol anchored inside b-cyclodextrin cavity gives the highest yield of 86.6% with variation in trans/cis ratio.

 

 

 

Balaraman Manohara & Soundar Divakar*

9
OC

191

 

Benzopyrans: Part 47– Reactions of 3-(b-di­methyl­aminoacryloyl)-1-benzopyran-4-one with some nitrogen nucleophiles

 

IPC: Int.Cl.7 C 07 P 311/04

 

The title pyranone 1 gives a mixture of pyridines 4 and 7 with ammonia, pyridine 5 and pyrazole 10 with phenylhydrazine, and pyridine N-oxide 8 with hydroxylamine.

 

 

 

 

Chandra Kanta Ghosh*, Sumit Kumar Karak & Amarendra Patra

 

10
OC

409

Synthetic and biological activity evaluation studies on novel isoxazolidines

  

IPC: Int.Cl.7 C 07 D 261/64 // A 61 P 31/04

 

A series of isoxazolidines have been prepared. Some of these compounds exhibit antioxidant and antibacterial activities. Enantioselective deacetylation studies on isoxazolidines using Candida rugosa lipase are also described.

 

 

Shubhasish Mukherjee, Raunak, Ashish Dhawan, Poonam, Ashok K Prasad, Carl E Olsen, Ashok L Cholli, William Errington, Hanumantharao G Raj, Arthur C Watterson & Virinder S Parmar*

 

11
OC

159

 

Studies on stereoselective synthesis of ethyl
anti-4-substituted phenyl-2-oxo-1,3-oxazolidine-5-carboxylates and their anti-bacterial activity

 

IPC: Int.Cl.7 C 07 D 263/00 // A 61 P 31/04

 

Ethyl anti-4-substituted phenyl-2-oxo-1,3-oxa­zolidine-5-carboxylates have been synthesized stereo­selectively from N-Boc-b-amino alcohols by O-tosylation followed by SN2 cyclization. All the compounds prepared are tested for their in vitro anti-bacterial activity against S. aureous, E.faecalis and E.faecium.

 

 

 

G Madhusudhan, G Om Reddy*, J Ramanatham & P K Dubey

 

12
OC

153

 

Potential plant growth regulators: Synthesis and activity of new substituted N-(2-benzoyl-4-chloro­phenyl)benzamides and N-[4-chloro-2-(a,a-hydroxyphenylmethyl)phenyl]benzamides

 

IPC: Int.Cl.7 C 07 C 233/07

 

 

 

Jaywant Govind Hatim & Vidya Joshi*

13
OC

174

 

1H NMR spectral studies of some 2,6-diaryl-4-aminothianes

 

IPC: Int.Cl.7 C 07 D 335/02

 

1H NMR spectra have been recorded for 4-amino-r(2),t(6)-diphenyl­thiane 5 and epimeric 4-amino­thianes 6a-8a and 6b-8b and analysed.

 

 

 

 

 

 

K Pandiarajan* & A Manimekalai

 

Notes

14
SCCB 164

Synthesis of pyrazoline and isoxazoline in triethanolamine medium

 

IPC: Int.Cl.7 C 07

Reactions of chalcones 1a-u with phenylhydrazine and hydrazine hydrate give pyrazolines 2a-u and with hydroxylamine hydrochloride yield iso­xazolines 3a-c in triethanolamine medium.

 

 

Nitin N Agrawal* & P A Soni

15
SCCB 081

 

Synthesis of 2-(coumarin-3-yl)-4-(chromon-3-yl)-benzopyrano[4,3-b]pyridines

 

IPC: Int.Cl.7 C 07 D 311/00

 

A series of new 2-(coumarin-3-yl)-4-(chromon-3-yl)benzopyrano[4,3-b]pyridines 3a-l have been pre­pared from coumarinoylmethylpyridinium bromide 1 under Kröenke’s conditions.

 

 

 

G Jagath Reddy*, C Thirupathaiah, D Latha, K Srinivasa Rao & Md Khalilullah

 

16
SCCB 101

A new route for the convenient synthesis of 3-aminomethyl-3,5,5-trimethyl-cyclohexanol

 

IPC: Int.Cl.7 C 07 C 13/18, 35/00

 

 

A new convenient route for the synthesis of 3- aminomethyl-3,5,5-trimethyl-cyclohexanol 5 and for two new intermediates 1,3,3-trimethyl-5-oxo-cyclohexane-carboxylic acid amide 3 and 5-hydroxy-1,3,3-trimethyl-cyclohexane-carboxylic acid amide 4, has been reported. Compound 5 has been identified as an important inhibitor of influenza virus fusion derivative and a potent and effective surrogate for the quinolizidine moiety.

 

         1                                    5

 

Satish C Pandey*, Sudhir S Singh, Balaram Patro & Anil C Ghosh

 

17
6944

 

A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenyl­methyl chloroformate as a coupling agent

 

IPC: Int.Cl.7 C 07

 

Synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc-amino acids and Fmoc-Cl as a coupling agent for peptide bond formation is described. The method is simple, efficient and rapid.

 

 

V V Suresh Babu* & S J Tantry

18
SCCB 175

 

A convenient synthesis of 1,2,4-triazolo[4,3-a][1,8]naphthyridines under solventless micro­wave irradiation

 

IPC: Int.Cl.7 C 07 D 401/00, 249/24

 

 

A simple and efficient method for the synthesis of
4-aryl-1-(2-pyridyl)-1, 2, 4-triazolo[4, 3-a][1,8]-naph­thy­ri­­dines using iodobenzene diacetate (IBD) under micro­wave irradiation is described.

 

 

K Mogilaiah*, S Kavitha & G Rama Sudhakar

19
SCCB 069

 

Microwave-assisted rapid synthesis of thiosemi­carbazide derivatives

 

IPC: Int.Cl.7 C 07 C 337/06

 

Rapid and highly efficient synthesis of thio­semi­carbazides by the coupling of isothiocyanate and carboxylic acid hydrazides in small amount of a polar solvent has been achieved under microwave irradia­tion by using a domestic microwave oven. The re­action proceeds rapidly, and is completed within 2-4 minutes giving a series of thiosemicarbazide derivatives 4-5(a-c) in high yields. All the compounds are fully characterized by FT-IR, 1H NMR, and mass spectroscopy.

 

 

Khosrow Zamani*, Khalil Faghihi, Shirindokht Bagheri & Mahdi Kalhor

 

20
SCCB 177

 

Unusual migrations and cyclization in the preparation of b-azido alcohols from b-hydroxy esters

 

IPC: Int.Cl.7 C 07 D 317/00

 

Migration of TBDMS and Boc groups from 2° alcohols to 1° alcohols during the reduction of b-hydroxy esters has been observed. Also, unusual cyclization has been noticed during tosylation of benzylic alcohol in tert-butyl((2R)-2-hydroxy-2-phenylethyl)carbonate with SN2 inversion.

 

G Madhusudhan*, G Om Reddy, J Ramanatham & P K Dubey

21
SCB 115

 

Synthesis and antimicrobial screening of certain novel Mannich bases bearing 1,8-naphthyridine moiety

 

IPC: Int.Cl.7 C 07 D 401/00 // A 61 P 31/04

 

 

A series of novel Mannich bases 4 have been prepared from (2-oxo-3-phenyl-2H-[1,8]naphthyridin-1-yl)acetic acid hydrazide 1 and screened for their antibacterial activity.

 

K Mogilaiah* & B Sakram

22
SCCB 159

 

Synthesis and antimicrobial screening of 2,4-diaryl-6-[2˘H-[1˘]-4˘-hydroxy-2˘-oxo-benzo­pyran-3˘-yl]pyridines and 2,6-diaryl-4-[2˘H-[1˘]-4˘-hydroxy-2˘-oxo-benzopyran-3˘-yl]pyridines

 

IPC: Int.Cl.7 C 07 D 213/00 // A 61 P 31/04

 

A facile synthesis of 2,4-diaryl-6-[2˘H-[1˘]-4˘-hydroxy-2˘-oxo-benzopyran-3˘-yl]pyridine and 2,6-diaryl-4-[2˘H-[1˘]-4˘-hydroxy-2˘-oxo benzo-pyran-3˘-yl]pyridines.

 

V V Mulwad* & D S Satwe

23
SCCB 139

 

New biologically active constituents from Terminalia chebula stem bark

 

IPC: Int.Cl.7 A 61 K 35/78 // C 07 D 311/32

 

Evidences are presented for the isolation and structures of two new compounds namely, 5, 7, 2'-tri-O-methylflavanone-4'-O-b- d-galactopyranosyl-(1 ® 3)-b-d-glucopyranoside 1 and 2a, 19a-dihydroxy-3-oxo-12-en-28-oic acid-28-oic acid-O- a -l-rhamno­pyranosyl-(1 ® 4)-b-d-glucopyranoside 2 from the bark of Terminalia chebula which are obtained along with known substances b-amyrin, lupeol and friedelin. Compound 1 displays antifungal activity while compound 2 exhibits both antifungal and antifeedant activities.

 

S K Srivastava* & S D Srivastava

24
OC

241

 

A new sesquiterpene lactone from Artemisia annua leaves

 

IPC: Int.Cl.7 C 07 A 61 K 31/00

A new rearranged farnesyloxy sesquiterpene lactone 1 has been isolated   from the  leaves of  Artemesia annua. The  structure  of   this compound has been esta­­blished as 5α-[3˘ (15˘),7˘ (14˘),11˘ (13˘)-trien]­pen­ta­decenyloxydihydrorteannuin B(1) on the basis of its spectral analysis.

 

Tarun Singh & R S Bhakuni*

 

 

                    Authors for correspondence are indicated by (*)

                    IPC: International Patent Classification

                    Int. Cl.: International Classification 7 edition, 1999