Indian Journal of Chemistry Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 43B NUMBER 12 DECEMBER 2004

CONTENTS

2623

Papers

Synthesis and characterization of {[(n-Buh Sn(02CCH=CHAr)hOh and crystal structure of {[(n-BuhSn(02CCH=CHPh)hOh

IPC: Int.CL7 C 07 C 13/20

Handong Yin*, Chuanhua Wang & Chunlin Ma

2628 Synthesis of some novel spiro heterocycles

IPC: Int.C1.7 C 07 D 239/00

Z=NH/O/S

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

Ten organotin compounds {[(n-Bu)2Sn (02CCH = CHAr)hO 12 have been synthesized by the reaction of (n-BuhSnO with ArCH=CHC02H in I: I molar ratio. The crystal structure of [[(n-Buh Sn(02CCH = CHPh)hO h is determined by X-ray single crystal diffraction.

A new class of spi ro pyrimidinetriones, thioxopyri­midinediones, pyrazolidinediones and isoxazoline­diones are prepared from dihydropyridine/pyran/thio­pyran dicarboxylates.

Jl

A~iX;o" Ar' z Ar'

X=O/S

R=HlCH.l

OVO

ArCO~ XCOAr

Ar' z Ar'

X=O/NH

2613

INDIAN J CHEM, 43B (12) 2004

2614

2635

2641

2646

CONTENTS

Synthcsis and mcsomorphic bchaviour of 3-[4-alkyloxyphcnyIJ-5-[3, 4-cthylcnedioxybellZyIJ-2-isoxazolines

IPe: Int.CL7 C 07 026/00

K II Umesha, K M L Rai *, Nagappa & J Mahadeva

Efficient synthesis of 1,2,4-triazolo[4,3-aj[I,8J­naphthy.-idines using nitrous acid under micro­wave irradiation

IPe: Int.CL7 C 070249/22

A simple homologous series of 3-[4-alky loxy phenyl] -5-f3,4-methy Icnedi oxybcnzy 1] -2-isoxazol i nes havi ng chiral sourccs havc been sy nthcs ized by thc rcac tion o f aldoximcs with safrole using ch loraminc-T. Thc sy nthcsized compounds cx hibit chiral ncmatic phasc (N*), smectic A (SA) and chiral smcc ti c phases (SC*).

where 11 = 4-14 7

A simple and efficient protoco l for thc synt hes is of I ,2,4-triazolo f 4,3-(/ HI ,S]naphthyridincs using nitrous ac id under mi crowavc irradiati on is dcscribed.

h NaN02 / CH)COOH •

MW NI-IN=CH-Ar

7

K Mogilaiah*, M Prashanthi & K Vidya

Microwave induced synthesis of 3/4-substituted-2-thioxo-/2-oxo-6-thioxo-l ,2,3,4,6,7 -hexahydro­thiazolo [4, 5-dJ py.-imidine and thiazole deriva­tives

IPC: Int.CL7 C 070239/00, 277/00

Vijay V Oabholkar* & Syed Sagir Ahmed

8

3/4-Substitutcd-2-oxo-6- thioxo- I,2,3,4,6,7-hexahydro­thiazolof4,5-d] pyrimidinc derivatives 3 , 3/4-substituted-2, 6-dithi oxo- l , 2, 3, 4,6,7 -hexahydrothia­zolof4,5-dJpyrimidine 4 and 4,5-substituted thiazolc derivati ves 6 havc been sy nthcsizcd by usi ng MW irrad iation tcchniquc, which g ives bCllcr y ic ld than the conventi onal method.

INOIAN J CHEM , 43B (12) 2()04

2650

2653

2661

CONTENTS

Microwave accelerated Pechmann synthesis of new isoxazolyl coumarins in dry media

A fa st and effici ent sy nthesis of isoxazo lyl coumarins 2 has been performed via the Pechmann react ion by mi crowave irrad iati on on solid support , montmorillo­nite K-I O, wh ich also acts as lewis acid catalys t. New isoxazolyl coumarin s have been prepared for the first time unde r dry conditi ons using microwave and by conventional method.

IPC: Int.CI.7 C 07 0 311/00

2

E Rajanarendar*, P Ramesh & K Ramu

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

T he electrochemical reduction of so me subst ituted 2-phe nyl-4-( 4' -ary lazophenyl )-3-t hioxo-2H-3, 4' -di­hydro-2, 4, 9, IO-tetraazaphe nan threne-l -ones has been studi ed over wide pH range.The kine tie parameters have also been studied.

IPC: Int.C1.7 C 07 0221/10

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

Qs N-{ n R oCSN-O-N=N-0 ~

N \ j

R = (a) H, (b) 4 '-CI, (e) 4'-OH , (d) 3'- C2Hs

Porcine pancreas lipase catalysed acetylation of ~-eyclodextrin anchored 4-1-butylcyclohexanol

Porc ine pancreas lipase ca tal yzed acetylation of 4 -1-

butylcyc!ohexanol anchored inside ~-cyc lodextrin

cavity gives the highest yie ld of 86.6% with vari ation in Irans/Cis ra tio . IPC: Int.CI 7 C 07 C 13/18

H H t-Uu H H

H H H

H OH

cis-4-I-butyleyc lohexanol

H H t-Uu H H

H H H

H H

Iralls-4-I-buty leyelohexanol

Balaraman Manohara & Soundar Divakar*

"'c,0, PPL .

DCD acetate

I~-BU-h--N-H P~CHJ

~ cis-4-t-buty lcyc lohexy l acetate

Ac, 0, PPL .

DCD acetate

t-Bu~ H~O~CH' H H H g

Iralls-4-I- butylcyc!ohexy l acetate

2615

INDIAN j CHEM, 43B (12) 2004

2616

2666

2670

CONTENTS

Benzopyrans: Part 47- Reactions of 3-(~-di­methylaminoacryloyl)-I-benzopyran-4-one with some nitrogen nucleophiles

fPC: Int.C!.7 C 07 P 311/04

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

(1(0) :::,... NMe,

R~ - MR Y

:7 N

:::,... I I I

° ° 1 R = H. Me OH ° °

4 Y=H 5 Y = NHPh

(Y°lrl R~NZ ~

o

:::,... I I R :7 I

Chandra Kanta Ghosh*, Sumit Kumar Karak & Amarendra Patra

Synthetic and biological activity evaluation studies on novel isoxazolidincs

IPC: Int.C!.7 C 07 D 261/64 II A 61 P 31104

o-{

° 7 Z = electron pair 8 Z=--O

° N-N Pl·, ......

10

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 .

OH o~

xi1' R' C~ 0 R' ,0 CRL> ):y1' I ~ N I ~ N + NN R ~ b R ~ b R 8 b

0 r

xii' CRL ) R' ,0 I ~ N

R ~ b 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*

xYJ:" R' ,0 I ~ N

R ~ b

0 r-

xii' . R .0

+ I "" N

R' ~ b

INDIAN J CHEM, 43B (12) 2004

CONTENTS

2683 Studies on stereoselective synthesis of ethyl anti-4-su bsti tuted phenyl-2-oxo-l ,3-oxazolidine-5-carboxylates and their anti-bacterial activity

IPC: Int.CI.7 C 07 D 263/00 II A 61 P 31104

Ethyl anti-4-substituted phenyl-2-oxo-I,3-oxa­zolidine-5-carboxylatcs have bcen synthesized stereo­selectively from N-Boc-~-amino alcohols by 0-tosylation followed by SN2 cyclization. All the compounds prepared are tested for their in vitro anti­bacterial activity against S. aureous, E.faecalis and E.faecium.

oJ< 0

HN~O HN~O ~OTOS _E_t3_N_/C_H_3_C-JI:~ (~~--(1(OEt

RN O~~t RN 0

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

2689 Potential plant growth regulators: Synthesis and activity of new substituted N-(2-benzoyl-4-chlorophenyl)benzamides and N-[4-chloro-2-(a,a-hydroxyphenylmethyl)phenyljbenzamides

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

CI

NHC=O

6~1 2 I A R 5 ~ 3

4

7a-1

Jaywant Govind Hatim & Vidya Joshi*

2696 IH NMR spectral studies of some 2,6-diaryl-4-aminothianes

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

K Pandiarajan* & A Manimckalai

(±) anti

NaBH

8a-i

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

6a-8a 6b-8b

2617

INDIAN J CHEM, 43B (12) 2004

26 18

2700

2702

CONTENTS

Notes

Synthesis of pynlZoline and isoxazoline in triethanolamine medium

IPC: Int.CI. 7 C 07 0261100,231100

3a-c

Nitin N Agrawal* & P A Soni

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

IPC: Int.CI.7 C 07 0311100

G Jagath Reddy*, C Thirllpathaiah, 0 Latha, K Srinivasa Rao & Md Khalilullah

Reacti ons of chalcones la-u with pheny lhydrazine and hydra7. ine hydrate give pyrazolines 2a-1i and wi th hydroxylamine hydrochloride yield isoxazol ines 3a-c in tri ethanolamine med ium.

TEA E

NHpH.HCI

R,YYR

N-C-CH=CH-o-~ R3 R2 II _.

o la-u

A series of new 2-(coumarin-3-y l)-4-(chromon-3-yl)benzopyrano[4,3-b]pyridines 3a-1 have been pre­pared from eoumarinoy lmethy lpyridin ium bromide 1 under Kroenke's condit ions.

R,

INDIAN J CHEM, 43B (12) 2004

2705

270S

2713

CONTE TS

A new rout e for the convenient sy nthesis of 3-aminomethyl-3,5,5-trimethyl-cyclohexanol

IPC: Int. C L7 C 07 C 13/1S, 35/00

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

A rapid and emcient synthesis of p-casomorphin employing fioc-amino acids and 9-lluorenyl­methyl chloroformate as a coupling agent

IPC: Int.CL 7 C 07 K 1100

A ncw convcnicnt route for the sy nthesis of 3-amino mcthyl-3.5 .5 -trimcthy l-cyc lohexanol 5 and for two new intcrmedi atcs 1.3.3-trimcthy l-5-oxo­cyclohcxanc-carboxy lic acid a midc 3 and 5-hydroxy-1,3,3-trimethy l-cyc lohcxanc-carboxy li c ac id amide 4, has bccn reponed . Compound 5 has bccn identifi ed as an impon ant inhibitor o f influc nza viru s fu sion deri va ti ve and a pote nt and cffec ti vc surroga tc for thc quino li zidine mo icty .

v o

1

Synthcs is o f p-casomorph in H-Tyr-Pro- Phe- Pro-Gl y­OH cmploy ing Boc-amino ac ids and Fmoc-C I as a coupling agent for pcptidc bond formation is descri bcd. The method is simple, c ffi cicnt and rapid .

Fmoc-CI, NMM Boc-Pro-OH + H-Gl y-OM e " )0 Boc-Pro-G ly-OMe ~ ~ ~ H-Tyr-Pro-Phe-Pro-G ly-OH

- IS C

v V Suresh Babu* & S J Tantry

A convenient synthesis of 1,2,4-triazolo[4,3-aJ[l,S]naphthyridines under solventless micro­wave irradiation

A simple and e ffi cie nt method for thc sy nthcsis of 4-aryl- I- (2- pyridy l)- I, 2, 4- tri azo lo[4, 3-a lll ,8 1-naph­thyridines using iodobenzcnc di ace tatc (IBO) under mi crowave irradiati on is dcsc ribcd.

IPC: Int. C L7 C 07 0401100,249/24

Ph I (OAel, -. cxxAr

D ?" ~ ~

I I "'..-; ..-;

N N NHN= CH N MW

3 4

K Mogilaiah*, S Kavitha & G Ra ma Sudhakar

2619

INDIAN J C H EM, 43B (12) 2004

2620

2716

2719

2724

CONTENTS

Microwave-assisted rapid synthesis of thiosemi­carbazide derivatives

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

R= a) 2-Pyridyl b) 3-Pyridyl c) 4-Pyridyl

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

+

Unusual migrations and cyclization in the preparation of J3-azido alcohols from J3-hydroxy esters

IPC: Int.CI? C 07 D 317/00

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

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

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

K Mogilaiah* & B Sakram

..

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-S(a-c) in high yields. All the compounds are fully characterized by Ff-IR, I H NMR, and mass spectroscopy.

W-NCS 3

t

MW. ~ U R-C-NHNHC-NHR'

4,5 (a-c)

R'= Benzyl and 2-methyl phenyl

Migration of TSDMS and Soc groups from 20

alcohols to 10 alcohols during the reduction of /3-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.

H

% o~

'Cq)o o A series of novel Mannich bases 4 have bcen prepared from (2-oxo-3-phenyl-2H-[ I ,81naphthyridin­I-yl)acetic acid hydrazide 1 and screened for their antibacterial activity.

~Ph

~.j( .. ,J" N7° nCR

CH2-CONHN I "Y ° N ~

I 1\ CH,-N X

- \~

4

INDIAN J CHEM, 43B (12) 2004

2727

2731

CONTENTS

Synthesis and antimicrobial screening of 2,4-diaryl-6-[2'H-[I']-4'-hydroxy-2'-oxo-benzopyran-3'-yl]pyridines and 2,6-diaryl-4-[2'H-[I']-4'­hydroxy -2' -oxo-benzopyran-3' -y I]py ridines

IPC: Int.Ct.7 C 07 D 213/00 II A 61 P 31104

v V Mulwad* & D S Satwe

New biologically active constituents from Termillalia chebula stem bark

IPC: Int.Ct.7 A 61 K 35/78 II C 07 D 311132

A facile synthesis of 2,4-diaryl-6-[2'H-[I']-4'­hydroxy-2' -oxo-benzopyran-3' -y l]pyridine and 2,6-diaryl-4-[2' H-[ I ']-4' -hydroxy-2' -oxo-benzopyran-3'­yl]pyridines.

4/1

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

8 9 0

, 3

2 1J \\ '~' OH \ 4 6 II

- , 0 " 5" 4 5 0 OH

1" HO ,, 0 3

OH

1

29 30 HO

25

HO,,2 8 15

3 27

22 l' 5 OH

COO/\-O~ 16 28 ur.~O

HO, OH .' 2

5

4 7 0 5

6

OH

23 24 2 OH

S K Srivastava* & S D Srivastava

2621

INDIAN J CHEM, 43B (12) 2004

2622 CONTENTS

2734 A new sesquiterpcne lac tone from Artemisia A new rearranged farnesy loxy sesquiterpene lactone 1 0/1/1110 leaves has been isolated from the leaves of /\rtelllesia

alln/la . The structure of th is compound has been IPC: InLCI .7 C 07 A 61 K 31/00 established as 5a-13' ( IY),7' (14') , 11' ( 13')-t rien] pen­

tadccenyloxydihydrortean nuin. 8(1) on the basis of its spectral analys is.

\0 """ .... ' ...... ,

"

"'O~ryvy

Tarun Singh & R S Bhakuni*

Authors for correspondence arc indi cated by (*)

IPC : Internationa l Patent Class ification Int. CI.: Internationa l Classification 7 ed ition, 1999

INDI AN J C HEM, 43B ( 12) 200~