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

VOL. 38B NUMBER 7 JULY 1999

759

763

766

CONTENTS

Rapid Communications

Biosynthesis of 4-methylcoumarin in Trigo-nella foellumgraecum

K Raj*, R S Kapil , H L Bhaumik & V KMahesh

The unusual behaviour of substituted I-aryl-2-(arylamino)ethanones towards Vilsmeier reagent

V J Majo, R Vijaya Anand & P T Perumal*

Tracer experiments prove that ethyl acetoacetate is a specific precursor of 4-methylcoumarin in TrigoneI/o foenumgraecum.

Me

~ ROVO~O 1 R= H 2 R=Ac 3 R=Me 4 R = Me; 3,4-dihydro

Reaction of l-aryl-2-(arylamino)ethanones with Yilsmeier reagent provides l-aryl-2-(N-formyl-N-arylamino)ethanones and not the expected l-aryl-2-N-formyl-N-arylamino)vinyl chloride.

o H ~N-Ar

Ar

* CI A~N-Ar

I CHO

Papers

Formal total synthesis of 2-pupukeanonc vicz radical mediated cyclisation of an enyne

A Srikrishna*, D Vijaykumar & G V RSharma

A tandem intermolecular and intramolecular radi cal ad-dition reactions sequence has been exploited for the for-mal total synthesis of 2-pupukeanone

(i) INDIAN J CHEM, 3S(7) 1999

771

777

CONTENTS

Stereoselective synthesis of oxiranes from substituted 4-piperidones and a tetrahydro-4-thiapyranone

The reaction of cis- I-methyl-2 ,6-diaryl-4-piperidolH:s and cis-2,6-diaryltetrahydro-4-t hi apyranone with di -azomethane affords the correspond ing oxiranes stcreosc-lectively.

o ~

Ar-;;;::1- R

X Ar

Ar

o

~'

..___,--J-- R X Ar

( X = NMe I S ; A r = aryt ; R = atky t )

V Vijayabaskar, S Perum:!':....*_&::..:',-'S:....=S..:.cl:....v..::a..:..ra:o.· fL' _______________________ _

Stcrcoselcctive chlorination of non-conjugatcd hetcrocydic alkcncs

Shadpour E M aHakpour* & Mohammad , Ii i',' lifigoic

Solid '1 na~c sy nthesis of diazepam hind ing if! lihitor fragmcnts 3:Z-J~ a nd 45-50 on a n cxible butancdioj d illlethacrylatc ': rosslinked polystyrene support

Oiels-Alder adducts or 4-suhst itut ed t ri azol i ncdionL's 1-1-Ph, 4-Il-Pr) with cyclopentadiencs and cyc lohcxali lL'llcs have been reacted with chlo rine Illo lecules In C: lrhOIl tetrachl oride solutior, . When n=Ph. cis-dichloridL's . 11\ ' obtained in :1 stereospec ili c lll:1nner. Whcn n=Il -Pr. ('J 1'. IrallS and rearrangement addu.:ts arc ohtained.

CI

. 0 C\ /1\ / ' T ~N~~,/ R V / /

(C~)n N~ C

n = 1 69~o (: is n ::. 1 : l' ;, ra ceme mxture n = 2 80% trans n =.!. 2CJ% tw 0 raceme mixtures

Solid nhase synthesis o r peptldes includi ng the hlo-aL' !: I'C sequences or dl

789

795

800

805

CONTENTS

Synthesis of an analogue of the naturally occurring Aristotelia indole alkaloid, fruti-cosoline

M A Hashem*, I Sultana & M A Hai

Synthesis of disaccharides related to human milk of antigenic properties

A synthesis of an analogue of the monoterpell uid indole alkaloid , fruti cosoline is repo ned.

Three disaecharides rel ated tu human milk ha ve been synthesized using tri chl oroaeetimidate g l yc()~ id atilln method .

AC~ OAe o AeO

OAc NH

AcO

~Ac5 ~o~z ----.~ BzO OR AcO 0 OAe NPhth

R = Me , R1 = H, R2= Ff = Bz R = A II , R1 = H , ~ = R3 = Bz

Rina Saksena, Desh Decpak* & Anakshi Khare

Photochemistry of some 1,4-dihydropyridinc d~rivatives : Part II

0, // C I CCI3 R = Me

R = AII

Irrad iati ons of Hantzsch esters unde r argun and ox ygcn atmosphere have been in ves ti gated.

R

HsC;p~nCO

810

814

818

CONTENTS

The investigation of nucleophilic reaction of antines with 3-bromo/chloro phthalide

R A Desai, S S Chaphekar & S D Samant*

Structure elucidation of two more metabolites of 7,8,9,IO-tetrahydroazepino [2,I-b ]quina-zolin-12(6H)-one, a potent bronchodilator: Part II

S C Sharma, U Zutshi & K L Dhar*

Synthesis of 4-thiazolidinone and 2-azetidi-none derivatives of 2-trifluoromethyl-l,8-naphthyridine as antibacterial agents

The reactions of 3-bromo/chloro phthalide with the ~cr ondary and aromatic primary ami nes in polar and n()n-polar solvents are described.

III vivo metabolic studies of the above melllioncd CO I11-pounds in rhesus monkey results in two more met a b()l i tc~ (A) and (B) . Structure of these compounds arc furthe r confirmed by their partial synthesis.

o

2~~;~8 3U:~

44a~5a6 7

1

, . / ":(C' :~O" 10 9 6, '

823

828

831

835

CONTENTS

A new amide, N-cinnamoylpyrrole and other constituents from Piper argyrophyllllm

Sangeeta Gupta, Amitabh Jha, Ashok K Prasad, Vivek K Rajwanshi, Subhash C Jain, Carl E Olsen, Jesper Wen gel & Virinder S Parmar*

Phytochemical invest igation of petrol and methanol ex-tracts of stems, leaves and fruit s or Piper argyro/Jhvlllll ll afford a new amide, N-cinnamoylpyrro1c together with twenty two known compounds including fourteen terpe-nes.

Notes

New sesquiterpene and other wnstituents from Artemisia arellaria

Wei Guo, Yan-Ping Shi & Zhong-.Jian Jia*

Synthetic modifications of ascomycin: Part III - A concise transformation of iso-ascomycin to 19,20-seco-deriyatives

R Zimmcr*, M A Grassbergcr, K Baumann, G Zenke & W Schuler

Facile oxidative cleavage of semicarbazone, tosylhydnllo.les and phenylhydraznnes with Oxone®

D Subhas Bose*, G Vanajatha & P Sriniyas

A new sesquiterpene 1 and ten known compound ~ have been isolated from the whole pl ants of Artemisia (/ 1"1' -/laria, and their structures estab li shed .

J0a, ~13

HO 15 12

6 R1=~=W=H, R2=R4=OH , R 6 = 01v1e 7 R1=~=W=H, R4= OH , R2=R 6 =01v1e 10 R1 = Rl= H, R4 = OH, f'l! = W= Ff= 01v1e

!f0 ~ CH

a l o "'/ Q.:< I 0 0 q o OH R

Q-I

()

An eflicient and mild method for the ox idati ve cleavage of semicarbazones. tosylhyd razones and phenyl hydra-zones using Oxone® is described .

(v)

~ HS05 /C~COOH R '\. C=:N--X • c= o

R1/ Pi / x = NHCCN~ or NKTs or NHAl

INDlAN.1 CHEM. 3N(7) ]999

837

839

843

CONTENTS

A short synthesis of tralls-3-methoxy-4,S-methylenedioxycinnamaldehydc, a metabolit e of Cassia grail dis

Dodda Rajasckhar & Gotlumukkala V Subbaraju*

Synthesis of some 4-aryl-1.2,3,4-tctrahydro-bcnzopyrano[ 4,3-d jpyrimidinc-2,S-diones/ pyrimidine-2-thioxo-S-ones

1a-e

D I llrahmbhatl*, Gajcndra II Raolji , Shashi U Pandya & Urvish R Pandya

2a-d

Reactions (If 1,4-bcnzolJuinone with aliphatic diamincs

Mcshah U Ahmad *, Koushik Saha, Taslima Mahmuda & Monira Yasmine

lralls-3-Methoxy-4,5-methylenedioxyci nn amaldcllydc has been synthesised from 2.

CH:!CHO , aq. NaOH

o't, 30 h 12%

0I'f)(CHO CHO

847

CONTENTS

Synthesis of pyrazolo[3,2-c ]cholest-4-ene de-rivatives from cholesterol

R K Tombisana & L Warjeet Singh*

Reaction of condensation products deri ved frol11 4-cholesten-3-one with hydrazi ne hydrate in ethanol af-fords pyrazolo[3 ,2-c]cholest-4-ene deri vative~ .

R= H, SCH3

!ISO Some reactions 01' 2-phenyl-4(3H)-quinazo- Rcaetion of 2- phcnyl-3. I-bcnzox:l7in-4H-onc wi th th io-

8S4

lillones carbohydrazidc affords 2- phcn yl -3-thiose l11l ca rhazi do-4(3H)"quin zo linone. The di azOIlIllin sa lt or 3-amino- 2-phenyl -4(3H)-qulllozo linone reacts with SOIllC ;lc ti vc methylenc compounds to yield th c correspo nding quin:lzo linone deriva ti ves.

Mohamed A Abdo*, Ibrahim F Zl~ id , Ga mal A El-Hiti & Olfat E Mahmoud

Decarbuxylative-halogenntion of alcuritic acid and its derivatives usi n!! N-hydnlxypvridine-2-thione and a halogen source

G B Suhramanian* & SOl1ldutta Sen

o 'I

0( ... NHN= CR f{! I N :::::,... N~Ph

Synthes is of some Cw (I)-halo compounds ohtaincd from :l!euriti c acid :lI1d its dc ri vnti ves (el !» hy dcc:lrho \\, I:I-live-halogenat ion uS ing N-hydroxypyntl inc-2- lh ionc " rCflorted (Bart lln'. proced ure).

HO,(H- {CH2lrCOOH I

HOCH- {CH2l s-CHzOH

t CH- (CH2l r CI 1\ Crl- (CH2)S- CH~H

HGCH- (CH2l r X I

HOCH- (CH2ls- CHzOH

X" CI. Br . i

8::7 All effi ci ent Knoevena gel con d('nsa~ i o ll u ~i)~!~ Knoevcn :lg,:1 C()ndc ll~ :lll(ln IS . l s~ i ql'd h \ lI LS :-d- ~ ,~c('ii!c HZSM-S zeoli te as a ctalyst ""herein ';l rtO ll ~ ;,r malic aideh)L:c\ IC:HI rL';"hly \\illt

"ul onnlllln ie ::nu cliwi L', "11l0 ,IL'ci:llc iI ' 1' !"(ldIlCI' ll lll e'-,pendi ng olefin iC proull cts.

:\ Iaiitl M Hcnlvi" , I\ !, l Il 1() ()U 'j':l' hak h"h, ____ -'I::.J.::::l"'-gl:.:l"'CI~ i\ l illl.lj"j-ani & Mitra ( ;!U1ssemz£ldeh _________ ____ _ _

( VI i ) NDTA I J CHE.M . 3S(7) 1999

859

861

865

867

CONTENTS

HZSM-5 zeolite as remarkable and reusable catalyst for the direct acetylation of alcohols and phenols under solvent-free conditions

Majid M Heravi*, Mahmood Tajbakhsh, Bagher Mohajerani & Mitra Ghassemzadeh

Facile PTSH-catalysed Beckmann rearrange-ment of ketoximes in solid state

S Ponnusamy & K Pitchumani*

Application of hexakisacetonitrile iron(III) perchlorate in organic synthesis

Niveta Jain & H G Krishnamurty*

Heterocyclic systems containing bridgehead nitrogen atom: Synthesis, stereochemistry and antimicrobial activity of cis-3,3a-dihydropyra-zolo[3,4-d]-s-triazolo[3,2-b lthiazoles

HZSM-5 zeolite catalyze the acetyl ation of alcohols and phenols with acetic anhydridc under so lvcntlcss system. The catalyst can be recycled with no acti vity loss .

HZSM-5 Zeolite ROH---------------.. ROOOCH3

Beckmann rearrangement of oximcs is found tu proceed very smoothly ill the presencc of Jlarct-tolucnesu lphoni c acid . In the case of benzophenonc oximc. th~ typc of product formed depends on tlie reaction tempcratun:.

o PTSH II

"!""!-""-'-+. C

R=R'= CH3

R = A1; R' = CH3 R=R'= A1

/" R NHR

Iron( lIl )perch lorate-CH1CN fu nction :lS an acid cata lyst and promotcs Rittcr reaction . The reagcnt is not sUltahle to bring about oxidative decarboxylat ion and clc;lVagc of glycols.

Arylidcne-s-triazolol3,2-b ]-6(5H)-ones 2 on trcatment with arylhydrazine furni sh 2.3-d iary l-cis-3 .3a-dihyd m-pyrazolo[3,4-d]-s-triazo lo[3,2-b )thiazoles 3.

1 1760 78 N

H N--N~ H N--N~\2 2 ,_~ 5' 6'1' 3a 3/ N- Ar ::«1 ~s CHAr ArNHNI-I- l~6 ~SH ' 3 4 ' ".. 5 4 H Ar H ~ H 4'~ 2' H

C~ CH3 2 3

Jag Mohan

869 Claisen-Schmidl condensation in the solid A simple and eftl cient sol id state synthesi , of 3-state cinnamoyl -2-methyl-1 ,8-naphthyridines 2 is described.

K Mogilaiah* & R Babu Rao

(vii i) INDIAN J CHEM, 3Xn (7) 1999

872

874

877

CONTENTS

Chemical examination of Tephrosia strigosa

E Vcnkata Rao* & P Sridhar

Studies on the Himalayan yew TaxllS wallichi-GI/a . Part VIII-Isolation of additional taxoids and ponasterone from the leaves of TaxlIs wallichialla

OA e

S K Chattopadhayay*, V Tripathi, A S Shawl, Raja Roy & n S Joshi

1 R = H ~R = Ac

New pentacycIic triterpenic esters from the roots of Calotropis gigalltea

M AIi* & .J Gupt::!

7-Hydroxy-2'-methoxy-4',S'-methylenediox yiso fla van 1 (astraciceran) and oleanolic acid 2 have been iso lated from the chloroform extract of Tephrnsia slrigo.l'tI .

A rare C-19 acetox ylated taxo id I . a brevifoliol deri va-tive 3 and ponastero ne 4 have been iso lated from the leaves o f T. wallichiallQ from Kashmir. The compounds are characterized on the basis of their physical ancl spec-tral data.

HO

HO

Phytochemical invest igation of the roots of Ca/olmpi.l' gigan lea results in the isolation of th ree new tritcrpeni c

esters identified as lup-l3(l S), 19(29)-dien-9a-yl acetate

1, urs-18~H-12, 20(30)-dien-3~-yl ace t:lte 6 ancl 17~hydroxy-28-normethylurs-18aH-1 2. 20(30)-d ien-3~-y l acetate 9.

( ix)

AcO 6, R = CH3 9, R = OH

IN DIAN J C HEM , 38(7) 1999

882

CONTENTS

Triterpenoid glycosidcs from Decaimea farge-sii Franch

Jie Kong, Xiaohui Yang, Runhua Lu, Yunpu Wang & Hanging Wang*

3-0-P-D-xylopyranosyl ( I ~ 3 )-u-L-rhamllopyrallosyl

( I ~2)-u-L-arabinopyranosy lhederagenill 2R-()-p-\)-

xylo-pyranosyl ( I ~4)-P-D-glucopyranosyl ( I ~6)-p-\)glu-copyranoside has been isolated from Dt'cai.l'llea F{{/'-gesii.

o ~

HO OH

o/roJO ~

HO OH

OH

Authors for correspondence are indicated by (*)

(x) INDIAN J C HEM, 3SB (7) 11)1)1)