CONTENTS 1153

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

VOL. 40B NUMBER 12 DECEMBER 2001

1163

CONTENTS

Rapid Communications

Ruthenium mediated oxidative fragmentation of the pinane system: An entry into chiral bicyclo[ 4.2.0]octanes

~Me Me

Me

~

Goverdhan Mehta*, K Subba Reddy & Jayant D Umarye

J'''~ o""~Me H Me OH

M6

0HMe

Me

+ J"" o '"'' 0

H

1166 Synthesis and carbonylation of aryl acetylenes

1170

ft° p~ .. FCOOH~: COOH I i I 11 I I H ~~~~~ +~ Reagents & Conditions : (i) DMF-POClyNaOH, (ii) PdCI2, CO, PPh3 , HCI

Sambasivarao Kotha*, Ahmed Tafesh, Kenneth Davenport & Philip Ortiz

A novel oxidative dimerization of acetylenes to conjugated dicarbonyl systems using iron (III) perchlorate

Acetylenes la-c, terminal as well as substituted, are converted into a, 13-unsaturated dicarbonyl systems 2a-c in good to excellent yields when reacted with iron (Ill) perchlorate (lTP) using acetonitrile as the solvent.

Ph-C=C-R

I a-e

rTP

Iv1eCN, 3 hr

~f.~ (R = H, Ph or Me) o

(A mixture of cis and trans isomers) II a-e

Kulbhushan Rana, Balbir Kaur, Harish Kumar, R D Anand* & Baldev Kumar*

INDIAN J CHEM, 40B (12) 2001

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1172

1174

1177

CONTENTS

8ase-catalysed rearrangement of terpinolene oxide

M A Pasha* & D Nagaraja

Synthesis of new hydantoins as intermediates for diamino acids

Terpinolene oxide. a tetrasubstituted spiro epoxide has been found to get rearranged over KOIBu in DMSO to give p-cymenol in high yields.

00

_KO_t_BU_._D_M_S0--l.~ _~ Reflux

Terpinolene oxide

2 OH

p-cymel 98%

An efficient and convenient procedure involving microwave and ultrasound conditions for the synthesis of 5.5-disubstituted hydantoins is reported.

o HI (NH4)2C03- 0 R

I-I:.?N COOH MW .• 2 min. )t~r

H () 2a-d

NH2COONH4. -ll..,N"Y KCN. )))). 3h. H O~ ~ H

HN-CO 1a-d 3a-d

S Thennarasu & P T Perumal*

Papers

New azasteroidal neuromuscular blocking agent possessing acetylcholine-like moiety in ring-A

Mange Ram Yadav*, Rajani Giridhar, Shivkumar P Rathod, Mukesh Mahatma & Prafulla M Sabale

A new neuromuscular blocking azasteroid 4 having acetylcholine-like fragment in ring-A has been synthesised by two different routes. The compound 4 has been found to be half as active as candocuronium on rat gastrocnemius s'ciatic muscle-nerve preparation. The chemical investigations leading to the synthesis of the title compound have been reported in detail.

eN, I Me 4

INDIAN J CHEM, 408 (12) 2001

1183

1187

1191

1196

CONTENTS 1155

Structural studies on a oxohexaene polyene antibiotic (HA-1-92) produced by Streptomyces CDRIL-312

S R Naik*, J Harindran & R K Nanda

Photocycloaddition of 2-aminoacrylonitriles to substituted l-acetonaphthones. Determination of the quenching rate constants

A new polyene macrolide antibiotic HA-l-92 has been isolated from the biomass of Streptomyces CDRIL-312 and subsequently used for chemical structural elucidation studies. Based on physicochemical properties. spectral studies (UV. IR. FfIR. HPLC. NMR and CIMS) and elemental analysis. HA-1-92 is found to be a new oxohexaene polyene macrolides and its probable chemical structure has been proposed.

28 26 24 22 20 18

eOOH

OH OH OH OH OH

Quenching of the triplet excited state of some substituted l-acetonaphthones by two captodative o1efins has been investigated.

~CN

X hv COCH, =< ---. =-- R CN + W

'3CO

CN

r' X ~I ~ +

H R Memarian*, M Nasr-Esfahani, H Gorner & DDopp

An efficient method nitration of phenols heterogeneous conditions

for chemoselective under mild and

Mohammad Ali Zolfigol*, Elahe Madrakian & Ezat Ghaemi

Micelle-catalyzed interaction between glycine and ninhydrin with and without added salts

Kabir-ud-Din*, Jamil K J Salem, Sanjeev Kumar & Zaheer Khan

R

X

Nitrophenols can be obtained via nirosation-oxidation of phenols with Mg(HS04h (I) or NaHS04.H20 (II) . NaN02 (III) and wet Si02 at room temperature in moderate to high yields.

lor II

III •

100% 0%

Catalytic effect of cationic micelles on the reaction rate of ninhydrin with glycine has been studied.

(eTAB/CPS, 70°C)

+ Product

INDIAN J CHEM, 40B (12) 2001

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]203

1207

]2]5

1219

CONTENTS

Synthesis, characterisation and X-ray diffraction studies of 8-(4-phenyl-2-awthiawlyl)-7 -hydroxy -4-methylcoumarin

P P Hankare, A H Jagtap, S S Chavan & P S Battase

Synthesis and antiinflammatory activity of new u-pyronochalcones, u-pyronoflavones and related products from 8-acetyl-umbelIiferone

M S Y Khan* & Sandhya Bawa

New 8-(4-phenyl-2-azothiazolyl)-7-hydroxy-4-methyl-cou marin has been synthesized by the diazotiza ti on of 4-phenyl-2-aminothiazole and its consequent coupl ing with 7-hydroxy-4-methylcoumarin.

Fourteen new sllbstituted u-pyronochalcones and fi ve u-pyronofl avanones have been obtained from 8-acety lumbelli fe rone. T he en one function of subst ituted u-pyronochalcones has been further exploited for synthesis of u -pyronofl avones, pyrazolines, isoxazolineslisoxazoles, di hydrofl avonollflavonol, aminoth iazole and the Mannich base. Evaluation of these compounds fo r an tiinfl ammatory activi ty against carrageenan induced rat' s paw edema shows encouraging results.

Four new alkaloids from Hypecollm Four new alkaloids, dihydroleptopine (±)-8-leptocarpum Hook. f.et Thomas

Bo-Gang Li, Min Zhou & Guo-Lin Zhang*

Three new compounds from Oxyria digYlla (L.) Hill

Yi Zhou, Guo-Lin Zhang*, Bo-Gang Li & Yao-Zu Chen

oxohypecorinine N-ox ide 2, demethyltoru losine N-methochloride 3 and hypecoleptopine 4, and known compound torulosine 5 have been isolated from Hypecoum leplOcarpum Hook. f. et T homs (Fan Fumariaceae). Their structures are elucidated based on spectra l evidence.

1223

1226

1230

CONTENTS 1157

Notes

Synthesis of some 3-cinnamoyl coumarin oximes and related cyclisation products derived from 3-acetylcoumarin

Min Ji, Jiaxing Hu, Weiyi Hua & Hongwen Hu*

A facile one step synthesis of some 3-trifluoromethyl-7 H-6(6/8, 6, 8-disubstituted-3-coumarino)-s-triazolo[3,4-b ][1, 3, 4] thiadiazines and 3-(2-phenyl hydrazino thiazolyl) coumarins

V Ravi Kumar & V Rajeswar Rao*

Synthesis of 2-substituted-quinoxaline 1, 4-dioxides

Jiaming Li, Min Ji, Weiyi Hua & Hongwen Hu*

3-AcetyIcoumarin reacts with aldehydes to form corres-ponding 3-cinnamoyl coumarins 2a-g. Oximation of 2a-g with hydroxylamine hydrochloride in ethanol and (or) isopropanol aqueous solution gives new coumarin oximes 3a-e or coumarin isoxazolines 4f-g.

o

~1-...;::°3 ~ --. ~R ~O~O o 0

~2 N

/' -...;:: A

~ I 0 0 4

Preparation of some 3-trifluoromethyl-7 H-6(6/8, 6,8-disubstituted-3-coumarino)-s-triazolo[3,4-b] [I, 3, 4]thia-diazines 1 and 3-(2-phenyl hydrazino thiazolyl)cou-marins 2 from 3-(2-bromoacetyl) coumarins has been described.

~R 00

R1 0 ~ N 't-NH- NH

2 S ©

Six new 2-substituted-quinoxaline I, 4-dioxides have been prepared by reacting benzofuroxan (BFO) with alkenes. The reaction has been proposed as a free radical mechanism.

o • CtNjR I" , .....-: ~ N + o

INDIAN J CHEM, 40B (12) 2001

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1234

1236

1239

CONTENTS

A new and general method Cor the synthesis oC quinoxalines

M Tajbakhsh, H Bakooie, M Ghassemzadeh, Y Sh Beheshtiha & M M Heravi*

A new Cacile and rapid synthesis oC acyl azides under solvent-Cree conditions

Shadpour E Mallakpour*, Abdol Reza Hajipour* & Ramin Vahabi

Synthesis of phthalocyanines crosswise-substituted with two alkylsulfanyl and two crown-ether

Salih Agirtas, Mehmet Sonmez, Mehmet Kandaz & Ozer Bekaroglu

Microwave-induced solvent-free, rapid and efficient synthesis o[ conjugated nitroalkenes using sulfated zirconia

B P Bandgar* & S P Kasture

A new alld geJ1Jeral synthetic method for the preparation of 2,3-disubstituted quinoxalines is described. Treatment of a-phenylenediamine with a-ketoaldoximes in ethanol affords 2,3-disubstituted quinoxalines in one-step reaction.

6' NH:! + 0.:::r R ----. r()rN:::r R ~NH:! HONJ-- R' ~N.J.R'

A rapid and simple method for the preparation of acyl azides is described. The reaction is carried out under solvent-free conditions.

° II Ar-C-CI

Silica gel ~

° II Ar-C-N:J

In this study, soluble phthalocyanines peripherally substituted with two amino and two alkylsulfanyl groups located crosswi.se have been synthesized and their reactivity has been examplified

1242

1245

1248

1251

1253

CONTENTS 1159

Synthesis of C,-Cl6"alkyl 2,3-dideoxy-glucosides from gl cose and fatty alcohols

Cr C 16-Alky l 2,3-dideoxyglucosides have been synthesized from glucose and Cr C IO-alkanols by using Ferrier reaction with boron trinuoride etherate (BF).Et20) as Lewis acid catalyst in key step.

HO~O a, b, e., AeO~ (O~O ...... ~O~" A:O~

OAe

~ AeO~OR OH OH OAe 2

"A'~ • ~~ . 5 OR 6 OR

S Konstantinovic*, J Predojevic, S Gojkovic, Z Ratkovic, B Mojsilovic & V Pavlovic

Allylation of cis-bicyclo(3.3.0)octane-3,7 -dione derivatives via fragmentation methodology

(a) AC20, NaOAc (b) HBr, AcOH (c) Cu-Zn (d) ROH (e), BF3. Et20 (I) NaOMe, MeOH

In troduction of allyl moiety in bicyc\o (3.3 .0)octane-3,7-dione derivatives using allyltributyltin is reported.

~ O~O

S Kotha*, R Sivakumar & E Manivannan

Cyclization of 2-ethylene ketal-cyclohexyl-l-propionamide in PPA-AcOH

N Srivastava*, A Kumar & C M Singh

Solid state deoximation with zinc chlorochromate: Regeneration of carbonyl compounds

AIBN

2-Ethylene ketal-cyC\ohexyl-l-propionamide on reaction with PPA/AcOH affords a new quinolone.

Aldoximes and ketoximes are oxidized with zinc chlorochromate in solvent-free condi tion at room temperature to furnish the corresponding carbonyl

~OH

~ A _Z_C_C_o_n_m_o_n_tm_o_r_il_lo_n:-ite::-:-K..,.-1_0-J.~ ~ A ~ room temperature, 1.5·8 hr ~

X X

S Balalaie, S H Salimi & A Sharifi*

An unusual oxidation of gramine methiodides under TaNOJDMF conditions

V Sridar*, R Maheswari & B S R Reddy

Gramine methiodides of a few indoles undergo an unusual oxidation under NaN02IDMF conditions to produce the corresponding indole-3-aldehydes.

OOHO

/' I " :-... N

H

INDIAN J CHEM, 40B (12) 2001

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1255

1258

1264

CONTENTS

Photooxygenation of some alkaloids by singlet molecular oxygen

fv1eO

Photooxygenation of papavarine, ephidri ne and nicotinic acid gives the products 2,4,5 and 7 respectively.

fv1eO

o CH3 C~ II I I

(PhC-CH-N)2 rsrCOOH 0'" ..... 0 ......

Shubha Jain*, Oeepali Pradhan & Amitbodh Upadhyaya

Ofv1e

Ofv1e

Montmorillonite KIO clay catalysed Baeyer condensation of heterocyclic aldehydes with N,N-dimethylaniline: Synthesis and photo-irradiation studies of heteroaryldiaryl-methanes

4 7

The montmorillonite KID clay catalyscd 8acyer conden-sation of a number of aromatic heterocyclic aldehydes 1-7 with N,N-dimethylaniline affords novel triarylmcthanes 8-14 in good yield. The tri ary lmethane 8 is irradiated at 325 nm for I hr under different solvent systems and the photoproducts are identified as 15 and 16.

~

1267

1270

1275

CONTENTS 1161

Semiempirical molecular orbital calculations of configurational properties of dihalogenated sulfur diimides

Mansour Zahedi*, Ahmad Shaabani & Mohammad Reza Shariat Zadeh

Synthesis and antibacterial activity of some new [1,3,4]oxadiazino[6,5-b] indoles and acetophenone hydrazones containing 1,8-naphthyridine moiety

(1a) EE

R, .yS~ N N

(1b) EZ

1 R

~S~N 1 1 R R

(1c) ZZ

A series of new 2-( 1,8-naphthyridin-2-one-3-yl)[ I ,3,4]oxadiazino[6,5-b] indoles 4 and acetophenone 1,8-naphthyridin-2-one-3-carbonylhydrazones 5 have been synthesized starting from 1,8-naphthyridin-2-one-3-carboxylic ac id hydrazide 1 and subjected to antibacterial activity studies.

o 0 II II

~C-NHNH:! '91 "C-NH~R

~t?--N.J:. 0 " 0")0-~ H 0 H

1 N'":tN" 3 R PH3 o:X ;,-. 1....-: R CO" C-NHN=C, :;....- I" 0 1 Ar "0 ~ 0

H 4 5 H

K Mogilaiah*, H Ramesh Babu & RBabu Rao

Synthetic and antibacterial studies rhodanine derivatives with indol-2,3-diones

R~O

V~I~ N 0 I H

R T Pardasani*, P Pardasani, D Sherry & V Chaturvedi

of A facile synthesis of new isatylidene and quinoline derivatives is described by treatment of rhodanine with indol-2, diones via Knoevenagel condensation and Pfitzinger reaction respectively .

INDIAN J CHEM, 40B (12) 2001

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1279

1282

1285

1287

CONTENTS

Aminothiazoles: Part 1--Syntheses and pharma-cological evaluation of 4-[isobutylphenylj-2-substituted-aminothiazoles

T Giridhar, R B Reddy, B Prasanna & G V P Chandra Mouli

A new sterol from Holarrhella alltidysellterica seeds

Ajay Kumar & Mohammed Ali*

'ew diterpenoid alkaloids from Delphinium souliei Franch

Lan He, Yuan Jiang Pan & Yao Zu Chen

Arabinoxylan from Cryptocarya wightialla Bark

Gudipati Muralikrishna & Rudrapatnam N Tha ranathan*

p-Isobutyl phenacy l chloride has been prepared by the reaction of chloroacetyl ch loride on isobu tyl benzene. It is condensed with th iourea and its derivatives to ge t the title compou nds.

A new sterol, named ho larrhenosterol, isolated from the seeds of Holarrhena anlidysenlerica along with p-sitosterol. has been charac terized as Sa-stiglTtasta-9( II ), 20(2 1 )-d ien-3p-ol on the basi s of spectral data analys is and chemical means.

H

Two new diterpernoid alkalo ids have been iso lated from Delphinilllll souliei Franch, and their structures estab li shed as Souline E and F on the basis o f spectral ev ide nces.

OMe .....-.'"""--" -OH

HO

Souline E Souline F

A homogeneous arabinoxylan (Ara-Xy l in 1.05: I ratio) has been obtained from the major water solu ble fraction of Crypotocarya wigiJlialla bark gum by employ ing gel filtration on Sephacryl S-400 and SE-HPLC techniques. Methylatio n of the pure polysaccharide followed by GLC-MS analysis reveals a highly substituted I A-linked xy lan backbone.

1289-1322 Annual Index

Authors for correspondence are indicated by (*)

INDIAN J CHEM, 40B (12) 2001