journal chemistry - niscair.res.in 38b(4) (contents).pdf · ing alcohol and acetate in high % ee....

__ >.It{dian Journal of Chemistry -.-~~- ~

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL 38B NUMBER 4 APRIL 1999

397

CONTENTS

Rapid Communications

Kinetic resolution of (±)-trans-3-acetoxy-2-phenyl-1,S-benzodioxapine by pig liver acetone powder

Pig liver acetone powder hydrolyzes trans-3-acetoxy-2- phenyl-1.5-benzodioxapine enantioselectively to produce the corresponding alcohol and acetate in high % ee. The assignment of thei r configuration is also described.

cc"'" 0J:.~ OAc PLAP, Ether ~ ~

o H ""Ph Phosphate buffer, pH 8

(±)-trans

cc"'" b~4 ~OH + ~ 2 3

o ""Ph IH

(+)[2S ,3R]

5

°14H cc"'" .",OAc ~ 2 3

P = Ph H (-)[2R,3S]

T Ganesh, K Kamalesh Sharma & G L David Krupadanam *

400 Zinc-induced novel reductive cyclodimerisation of some a,!3-unsaturated ketones

Ar~Ph

o

Sankar P Dey & Asok K Malik*

403 Novel euglycemic and hypolipidemic agents : Pyridine containing unsaturated thiazolidinediones

B B Lohray,* V Bhushan, A Sekar Reddy, P Bheema Rao, N J Reddy, K A Reddy, K R Vikramadithyan & R Rajagopalan

(i)

Some a ,!3-unsaturated ketones are found to undergo zinc-induced novel reductive cyclodimerisation yielding substi tuted cyclopentanols as major products.

Ph I

Zn dusl it Art;(H ._---c= q... Ar~O Ph

THF -H 2 H + r.t. . 10 h . A r"'" . '''''0/ A r Ph

Ph 0

Several pyridyl containing thi azolidinediones having cyclic amines as linker have been synthesized and evaluated for their eugl ycemi c and hypolipidemic acti vities. Compound 6a-maleate has been found to have an excellent pharmacological profile.

6a W = CH2

6b W =CH20

INDIAN J CHEM, 38B(4) 1999

CONTENTS

Papers

407 Synthesis and Na+llr exchange inhibitory activity of . indanylideneacetylguanidines

N V S Ramakrishna,* A K Jain, A V Ghate, R D Gupte & R V S V Vadlamudi

413 A quantum-chemical study on bi (1,2,3-triazole) molecule

Riza Abbasoglu*, Necdet Saltek & A Aykut ikizler

418 Convenient and simple synthesis of N-{[9H-fluoren-9-yl)methoxy]carbonyl}-(Fmoc) protected ~-amino

acids (=homo-a-amino acids) employing Fmoc-aamino acids and dicydohexyl carbodiimide (DCC) mixtures

K Ananda & V V Suresh Babu*

(ii )

Synthesis and Na+/H+ exchange inhibitory acti vi ty o f indanylideneacetylguanidines 7, 8 has been described ,

The conformational analys is of 4,4'-bi ( I H- I ,2,3 -triazo le) A, 5,5 'bi(l H- I ,2,3-triazo \e) B and 5,5'-bi(2H-1 ,2,3-tri azole) C tautomers o f fl ex ible bi ( I ,2,3- tri azole) molecule containing various reaction centres has been perfo rmed by semiempirical methods AM I and PM3,

IP = 0° 1

IP = 0° 1

IP = 0° I

A

B

C

I H 4'

)j~~ :: 4 If I'

IP = 1800

2

H I 4'

?'N~N --:: N " - ~ .

I 5 5~ I ?, "\ N :::::- . __ N _ - 4 I ' 'H

IP = 180° 2

The ho mologation of a-amino acids to ~-amino acids can be carried out lI sing the mi xture o f Fmoc-a-amino acids and DCC. The resulting Fmoc-amino acid diazoketones upon wolff rearrangement gi ve Fmoc-~ -homoamino acids in good yield,

Fmx;- NH-CHR-C(X)H + occ

1 CH

2N

2

Frmc' NH-CHR-COCHN2

1 PhCOOAgI dV><lne- warer, 70C

C

Fmx'NH-CHR-CH2- COOH


CONTENTS

424 Synthesis of ovalichromene-B, a naturally occurring The synthesis of ovalichromene-B has been described. pyranoflavanone

0--

bo KOH

3 + ~ \ ---I~~ -~ EtOH

CHO

M Arnzad Hossain

4 Demethoxy methy lation ------.. ~ 5

NaOAc ~

EtCH

o

6

427 Synthesis of 3', 5, 7-trihydroxy-6 ", 6"-dimethylpy- The synthesis of 7 has been described. rano[2", 3" .4', 5']flavanone

HO

M Arnzad Hossain

OH 0

7

431 Synthesis of 5-hydroxy-7-methoxy-8-C-prenylflava- The synthes is of 5-hydroxy-7-methoxy-8-C-prenylflava-

434

none none 7 is described.

M Amazad Hossain

Synthesis of benzimidazo[l , 2-c]quinazolines as possible bronchodilators

A Raghu Ram Rao· & Rajesh H Bahekar

(iii)

OH 0

7

Synthesis of some 6-aryl-benzi midazo[ I , 2-c ]quinazolines has been criti call y investigated using three different methods. The bronchodilatory act ivity of compounds is reported usi ng ill vitro and ill vivo animal s models.

X«N:@ o N NJ- Ar

x

INDIAN J CHEM, 388(4) 1999

440

445

452

CONTENTS

Synthesis of azetidi~ones and thiazolidinones from hydrazinopyrimidine as po~ential antimicrobial agents

J M Parmar,.J J Modha & A R Parikh*

Synthesis and antimicrobial activity of some nitrogen heterobicyclic systems: Part I

H A Allimony*, H A Saad & F A A EI-Mariah

Fused heterocycles: Synthesis and fungistatic activity of some ] -aroyVaryloxyaceto-4-aryl-5-cyano-3-methylpyrazolo[3, 4-b ]pyridin-6-ones and l-aroyVaryloxyaceto-4-aryl-3-methylpyrazolo[ 4, 3-e]pyrido[J , 2-a]pyrimidines

Formati on of 2-azetidi nones 5a-g and 4-thiazolidinones 6a-1 have been reported from 6-p-anisyl -S-cyano-2-hydrazino-3-N-methyl-3, 4-dihydropyrimidin-4-one 3. The compounds have been evaluated for their antimicrobi al activity.

o

-OJCc CH3 N'

H3CO 'I ~ I ~ - N NH

I

N 0yR 5 CI

A number of biocidal nitrogen heterobicycli c systems 2-20 have been synthesized and their structures have been deduced on the basis of elemental analysis, IR , IH NMR, UV and MS data.

1

i) Ar 'NHNH2

ii ) NaOH ii i) HCHO

iv) Ar ' NHNH2

v) FeCI} ~

20a

Synthesis of 3 and 4 vi a Mi chael addition between 2 and ethyl cyanoacetate/2-amin opyrid ine is described.

R-g~NN N CH, '-::-~1t~R ° H R' ~

CN

R-C-N-N

. r--~~H3 ---..[~ N R

Mukhtar Hussain Khan, Raziul Haque,

Taruna Agrawal, Ahmad Safi &

Nizamuddin*

3 2

(iv )

4

INOlAN J CHEM, 388(4) 1999

457

461

CONTENTS

Two new sphingosine derivatives from Sinlliaria crassa Tixier-DurivauIt of the Andaman and Nicobar Islands

Two new sphingosine derivatives, N-hexadecanoyl-I , 3-dihydroxy-2-amino-4, 8-octadecadiene 1 and N-henicosanoyl-I, 3, 4-trihydroxy-2-amino-tetradecane 5 have been isolated from a soft coral Silllliaria crassa of the Andaman and Nicobar Islands.

I

9H YH20H \l

H3C-(CH2h-CH2-CH=CH-CH2-CH2-CH=CH-CH-CH-NH-C-CH2-(CH2)13-CH3 18

21 '

V Anjaneyulu* & P Radhika

8 4 3

1

OH

................................ ...t4.1 J.. 14- '-/ '-/ '-/ ~ 1 312 'OH

OH NH

5

Notes

. , . 2 2 16

A convenient and highly diastereoselective synthesis of optically active sullinate esters from sulfonyl chlorides under solid state conditions

A manupulatively simple and rapid method for synthesis of chiral sultinate esters 1 and 2 is described.

Abdolreza Hajipour* & Fereshteh Islami

o \I

R-S-O \I o

( eO 0 0 .

M )3P

" ",.," " .JI + R'OH -----i.. S··, + S/ Silica gal R/ 'OR' R ....... "' OR '

1-(5) 2 -( R)

R' = menl hy l

R = Aryl

463 LPDE catalysed rate acceleration of Diels-Alder The Diels-Alder reaction of dienes 1, 2 is described, reaction of electron-deficient dienes with ill Sitll

generated2-methoxycarbonyl-p-benzoquinone

S Paul, V Srivastava, S Ray & S N Suryawanshi*

(v)

0

(lI' 0

E= COOMe

+

1 2

O)R 0 COR

--------~ \PI • R=OMe 0 • R = O-Menthyl


466

470

473

CONTENTS

Chemoselective electrooxidation of (E)-I-phenyl-2-(phenylthio)ethylene and l-phenyl-2-(phenylthio)acetylene

S Ramalingam, S Perumal*, S Selvaraj & S Sivasubramanian

A new synthesis of I, 4/1, 5-dioxanocoumarins

OH

H0-«X0 0 ::,....1 h

R

N Gangadhar, Ch Harish Kumar & G L David Krupadanam*

R'

Synthesis of some new type of thiazolyl coumarins

K Srimanth & V Rajeswar Rao*

(vi)

Electrooxidation of (E)- I-phenyl-2-(phenylthio)ethylene (PPTE) and l -phenyl-2-(phenylthio)acetylene (PPTA) on g lassy carbon electrode (GCE) in acetonitrile medium furni shes the corresponding sulphones chemoselective ly.

FIl7 ~s-D V-C=C-S~

o H

PP1E PPTA

7, 8-Dihydroxycoumarins on reaction with epichlorohydrin in the presence of acetone- potass ium carbonate give I , 4- and I , 5-dioxanocoumarins in good yields.

Synthesis o f [3-(2-hydrazino-4-thi azolyl)coumarino] phenylmethyl methines 1 and [3-(2-amino-4-thiazolyl)coumarino]diamino methi nes 2 is reported.

~Rl00

20 h R N

Jl ':I CH3 S N-N~

1 0 3 R

R h N R~~O 0

Jl NH2 S N=( H

2 N 2


476

479

482

CONTENTS

A facile one-step synthesis of 3-substituted and 1-methyl-3-substituted-2H -naphtho-[2,3-e ] [1,4]diazepin-2, 5(1H, 4H)-diones

K Rama Devi & M Satyanarayana Reddy*

Synthesis of 5, 8-dimethyl-2-tetralone, an intermediate for occidol

M T Bachute*, C H Gill, K N Ganage & R T Bachute hute

Mild and efficient synthesis of triaryl cyanurates by using effective combination of tetrabutyl ammonium bromide and dibenzo-(18)-crown-6

R K Sharma & M M Salunkhe*

(vii)

Title compounds 2 have been synthesised by the condensation of 2H-naphth[2, 3-d][3, l]oxazin-2, 4(lH)-dione (1; R=H, CH,) with a -amino acids in hot acetic acid.

An intermediate for occidol 7 has been synthesized in si x steps starting from p-anisaldehyde I .

o£X? 7

2, 4, 6-Triaryloxy-I , 3, 5-triazine (tri arylcyanurates) have been synthesized in high yield under mild reaction conditions by treating cyanuric chloride with the potassium salts of phenols in a two phase system consisting of chloroform, water and effective catalytic mixture of tetrabutyl ammonium bromide and dibenzo( 18)-crown-6

KO- Ar Water I CH03

TBAB & DB -(18)- C - 6

3


484

488

491

CONTENTS

Photochemical reaction between ascorbic acid and silver(I) in aqueous Triton x-tOO and its analytical application

Anjali Pal

Photochromic fulgides: Part 3 - Synthesis and some photochemical reactions of diphenylmethylene substituted methylenesuccinic anhydrides

Abdullah Mohamed Asiri* & Salih Salem AI-Juaid

Synthesis and biological evaluation of some sterically hindered 4-[2 '-benzo(b)furanyl]coumarins

Imthyaz Ahmed Khan & Manohar V Kulkarni*

(vii i)

A ne w spectrophotometric method for ascorbic acid determination is described . This ut il ises the photochemical reaction of ascorbic acid with silver(l) in Triton X- IOO (TX-IOO) medium with the production of yellow silver sol (I"01ax=415 nm). The method is quick, simple and reliable and applicable fo r the analys is o f vitamin C in pharmaceutical preparatio ns.

The pale yellow crystals of ful gides Sa, 5b, 5c, 5d and 5e in crystalline state and in solutions, change to red on irradiation at 366 nm; thi s change is reversed on ex posure to white light. The substituents o n the methylene group have a remarkable e ffect on the absorption maxima of both the coloured and uncolo ured forms.

PhXPh

0 0 R\

I R2 . 0

Various sterica lly hinde red benzofuranyl coumarins have been synthesised by the reaction o f 4-bromo methyl coumarins with ()hydroxy acetophenones and methyl salicylate. Their contiguration have been establi shed by 10 d iffe rence NOE spectra.

or DIOXANE

R


495

501

505

CONTENTS

Synthesis and antimicrobial activity of I, 8-naphthyri-inyl-4-thiazolidinonesll,3-thiazin-4-onesl2-azetidinones

K MogiJaiah*, P Raghotham Reddy & R Babu Rao

Synthesis and fungicidal activity of some 2-arylamino-I, 3, 4-thiadiazino[6, 5-b]indoles and 2-aryl-I, 3, 4-oxadiazolo[2, 3-cJ-I, 2, 4-triazino[5, 6-b]indoles

Nizamuddin*, Mukhtar Hussain Khan, Shafqat Alauddin & Raziul Haque

3

Synthesis and evaluation of anti-inflammatory activity of 2-(4-isobutylphenyl)propionyl derivatives of amino acids and peptides.

S L Belagali* & M Himaja

(ix)

Synthesis of 2-aryl-3 -[p-( I . 8-naphthyridin-2-yl)phenyIJ-4-thi azolidinones 6. 2-aryl -3-[p-( I. 8-naphthyridin-2-yl)phenyll - l . 3-thi azin-4-ones 7 and 4-aryl-3-chloro-I -[p-( I. 8-naphthyridin-2-yl)phenyl]-2-azetidinones 8 is described . The antimicrobial behaviour o f these compounds has been studied.

CO--o-'-': .... I '" 'I ~ .~TAr

N N --?--\ 8 0 CI

Indoles 3 and 6 have been synthesized by cyclization of isatin-3-(arylthiosemicarbazones) and isatin-3-(5-aryl- l . 3. 4-oxadi azol-2-yl)hydrazones with conc. H2S04•

A series o f new 2-(4 -isobutylphenyl)propionyl amino acids and peptidcs have been synthesized and subjected to anti-inflammatory activity studies. All the compounds are active as compared to the standard drug ibupro fen.


508

511

515

CONTENTS

New derivatives of isoniazide, pyrazinamide and 2-aminobutanol and their anti-tubercular acti; ity

"

C V Shabadi, B A Shelar & A R Shelar*

Synthesis of 8-(3' -butenyl)-9, 9-dimethyl-2-oxaspiro[4.4]non-7 -en-I-one, an advanced intermediate for terpenes of the marine sponge Dysidea herbacea

Anjan Ghatak & Subrata Ghosh*

Microbial oxidation of a-pinene to (+ )-a-terpineol by Candida tropicalis

T Chotterjee, B K De & D K Bhattacharyya

(x)

Some new s- tri azine derivatives having isoni azide, pyrazina mide and 2-aminobutanol moiety have been synthesized by condensation of substituted s-triazines with isoniazide, pyrazinamide and 2-aminobutanol.

Where R =

R-X

(X=H)

CONHNH-

0" N

N~ONH- N H

( Jl 0 r C 2 H 5- ~ H - C H 2 0 H N

The synthesis of the title compound 6 from the keto-ester 12 is described for entry into terpenes of marine sponge Dvsidea herbacea.

12 6

Microbial oxidation o f a-pinene to (+)-a-terpineoJ by Calldida lropicalis is reported.

C.lropicalis 9 o • 30 C, 4 day s

OH


518

521

CONTENTS

Triterpenoidal glycosides from the seeds of Dedrocalamus StrictllS

H

Renu Rai*, I R Siddiqui & J Singh

Two new O-~-D-glycosides from the stem bark of Cassia javanica

Rashmi Sanghi*, Rahul Singh & J Singh

Two new triterpenoidal glycosides 3~, 21~ , 28-trihydroxyolean-12-en-28-0- (~-D-arabinopyranosyl- ( 1---73) )-D-arabinopyranosyl(1---73)-~-D-arabinoside and 3~, I 9a-dihydroxyurs-12-en-28-oate-3-0-~-D-arabinopyranoside have been isolated from the seeds of plant Dendrocalamus strictus,

O:JOHH

OH O¥ ~OH 0 /{O OH

o OH

C H 20

OH

Two new glycosides, l-hydroxy-3 , 6 , 7, 8-tetramethoxy-2-methylanthraquinone-I-O-(2 "-O-~-D-mannopyranosyl)-~-D

allopyranoside and 2a, 3~ , 19a-trihydroxy-olean-12-en-28-oic acid-28-0-~-D-xylopyranoside have been isolated from the stem bark of Cassiajavanica,

-===-:::--Authors for correspondence are indicated by Y'~ _: ~)

%:,,",\0 ' ., { I . !.,~

~ r- __ .- _ \ \.-\lJ t .\{ 1 ' 40~.

"r - t'l O - '}' )

0" " . 0(.\1<"'" !J '""H '" /J

' ~ ... -:. ~ .... / /'"

~--~ (x i) INDIAN.T CHEM, 388(4) 1999

journal chemistry - niscair.res.in 38b(4) (contents).pdf · ing alcohol and acetate in high % ee....

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