Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 40B

NUMBER 12

     DECEMBER 2001

CONTENTS

Rapid Communications

 

 

 

1163

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

 

 

 

 

 

 

 

 

Goverdhan Mehta*, K Subba Reddy &
Jayant D Umarye

 

Text Box:

 

 

 

 

 

 

1166

Synthesis and carbonylation of aryl acetylenes

 

 

 

 

 

 

 

 

 

 

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

Text Box:

 

 

 

 

 

 

1170

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

 

Acetylenes 1a-c, terminal as well as substituted, are converted into a, b-unsaturated dicarbonyl systems 2a-c in good to excellent yields when reacted with iron (III) perchlorate (ITP) using acetonitrile as the solvent.

 

 

 

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

 

 

 

 

 

 

1172

Base-catalysed rearrangement of terpinolene oxide

 

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

 

 

 

M A Pasha* & Nagaraja

 

 

 

 

 

 

 

1174

Synthesis of new hydantoins as intermediates for diamino acids

 

An efficient and convenient procedure involving microwave and ultrasound conditions for the synthesis of 5,5-disubstituted hydantoins is reported.

 

 

 

S Thennarasu & P T Perumal*

 

 

 

 

Papers

 

 

 

1177

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

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 sciatic muscle-nerve preparation. The chemical investigations leading to the synthesis of the title compound have been reported in detail.

 

 

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

 

 

 

 

 

 

 

1183

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

A new polyene macrolide antibiotic HA-1-92 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, FTIR, 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.

 

 

S R Naik*, J Harindran & R K Nanda

 

 

 

 

 

 

 

1187

Photocycloaddition of 2-aminoacrylonitriles to substituted 1-acetonaphthones. Determination of the quenching rate constants

Quenching of the triplet excited state of some substituted 1-acetonaphthones by two captodative olefins has been investigated.

 

 

H R Memarian*, M Nasr-Esfahani, H Görner & D Döpp

 

 

 

 

 

 

 

1191

An efficient method for chemoselective nitration of phenols under mild and heterogeneous conditions

Nitrophenols can be obtained via nirosation-oxidation of phenols with Mg(HSO4)2 (I) or NaHSO4.H2O (II), NaNO2 (III) and wet SiO2 at room temperature in moderate to high yields.

 

 

Mohammad Ali Zolfigol*, Elahe Madrakian & Ezat Ghaemi

 

 

 

 

 

 

 

 

1196

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

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

 

 

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

 

 

 

 

 

 

 

1203

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

 

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

New 8-(4-phenyl-2-azothiazolyl)-7-hydroxy-4-methyl-coumarin has been synthesized by the diazotization of 4-phenyl-2-aminothiazole and its consequent coupling with 7-hydroxy-4-methylcoumarin.

 

 

 

 

 

 

1207

Synthesis and antiinflammatory activity of new a-pyronochalcones, a-pyronoflavones and related products from 8-acetyl-umbelliferone

 

 

 

 

 

M S Y Khan* & Sandhya Bawa

Fourteen new substituted a-pyronochalcones 4a-n and five a-pyronoflavanones 5a-e have been obtained from 8-acetylumbelliferone. The enone function of substituted a-pyronochalcones has been further exploited for synthesis of a-pyronoflavones 6a-e, pyrazolines 7a-c, isoxazolines/isoxazoles 8a-c, dihydroflavonol/flavonol 9a-b, aminothiazole 11 and the Mannich base 12. Evaluation of these compounds for antiinflammatory activity against carrageenan induced rat's paw edema shows encouraging results.

 

 

 

 

 

 

1215

Four new alkaloids from Hypecoum leptocarpum Hook. f.et Thomas

Four new alkaloids, dihydroleptopine 1 (±)-8-oxohypecorinine N-oxide 2, demethyltorulosine N-methochloride 3 and hypecoleptopine 4, and known compound torulosine 5 have been isolated from Hypecoum leptocarpum Hook. f. et Thoms (Fan Fumariaceae). Their structures are elucidated based on spectral evidence.

 

 

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

 

 

 

 

 

 

 

1219

Three new compounds from Oxyria digyna (L.) Hill

The structures of three new compounds isolated from the whole plants of Oxyria digyna (L.) Hill have been elucidated to be oxytriaflavonol 1, 5, 7, 3-trihydroxy-4'-methoxyflavanone-7-O-b -d-glucopyranosyl-a-l-rhamno-pyranoside 2 and 5, 7, 2', 3', 4'-pentahydroxyflavone-8-C-
glucopyranoside 3 on the basis of spectral data. Five known compounds isolated have been determined to be vitexin 4, orienin 5, heperedin 6, quercetin-3-O-
b-d-glucopyranoside 7 and stigmasterol 8.

 

 

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

 

 

 

 

Notes

 

 

 

1223

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

3-Acetylcoumarin reacts with aldehydes to form corresponding 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.

 

 

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

 

 

 

 

 

 

 

1226

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

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

 

 

V Ravi Kumar & V Rajeswar Rao*

 

 

 

 

 

 

 

1230

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

Six new 2-substituted-quinoxaline 1, 4-dioxides have been prepared by reacting benzofuroxan (BFO) with alkenes. The reaction has been proposed as a free radical mechanism.

 

 

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

 

 

 

 

 

 

 

1232

A new and general method for the synthesis of quinoxalines

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

 

 

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

 

 

 

 

 

 

 

 

1234

A new facile and rapid synthesis of acyl azides under solvent-free conditions

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

 

 

 

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

 

 

 

 

 

 

 

1236

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

In this study, soluble phthalocyanines peripherally substituted with two amino and two alkylsulfanyl groups located crosswise have been synthesized and their reactivity  has been examplified through the formation of a Schiff's base with benzo-15-crown-5 aldehyde.

 

 

Salih Ağirtas, Mehmet Sönmez,
Mehmet Kandaz & Özer Bekaroğlu

 

 

 

 

 

 

 

1239

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

Sulfated zirconia catalyzed synthesis of conjugated nitroalkenes has been carried out under solvent-free condition using sulfated zirconia. Recyclability of catalyst, isolation of pure products by simple filtration and evaporation are important features of this method.

 

 

B P Bandgar* & S P Kasture

 

 

 

 

 

 

 

1242

Synthesis of C7-C16-alkyl 2,3-dideoxy-glucosides from glucose and fatty alcohols

C7-C16-Alkyl 2,3-dideoxyglucosides have been synthesized from glucose and C7-C10-alkanols by using Ferrier reaction with boron trifluoride etherate (BF3.Et2O) as Lewis acid catalyst in key step.

 

(a) Ac2O, NaOAc (b) HBr, AcOH (c) Cu-Zn (d) ROH (e), BF3.Et2O (f) NaOMe, MeOH

 

S Konstantinovic*, J Predojević, S Gojković, Z Ratković, B Mojsilović & V Pavlović

 

 

 

 

 

 

 

1245

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

Introduction of allyl moiety in bicyclo (3.3.0)octane-3,7-dione derivatives using allyltributyltin is reported.

 

 

S Kotha*, R Sivakumar & E Manivannan

 

 

 

 

 

 

 

1248

Cyclization of 2-ethylene ketal-cyclohexyl-1-propionamide in PPA-AcOH

 

N Srivastava*, A Kumar & C M Singh

2-Ethylene ketal-cyclohexyl-1-propionamide 8 on reaction with PPA/AcOH affords a new quinolone 9.

 

 

 

 

 

 

1251

Solid state  deoximation with zinc chlorochromate: Regeneration of carbonyl compounds

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

 

 

S Balalaie, S H  Salimi & A Sharifi*

 

 

 

 

 

 

 

1253

An unusual oxidation of gramine methiodides under NaNO/DMF conditions

Gramine methiodides of a few indoles undergo an unusual oxidation under NaNO2/DMF conditions to produce the corresponding indole-3-aldehydes.

 

 

V Sridar*, R Maheswari & B S R Reddy

 

 

 

 

 

 

 

1255

Photooxygenation of some alkaloids by singlet molecular oxygen

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

 

 

Shubha Jain*, Deepali Pradhan &
Amitbodh Upadhyaya

 

 

 

 

 

 

 

1258

Montmorillonite K10 clay catalysed Baeyer condensation of heterocyclic aldehydes with N,N-dimethylaniline : Synthesis and photo-irradiation studies of heteroaryldiarylmethanes

The montmorillonite K10 clay catalysed Baeyer condensation of a number of aromatic heterocyclic aldehydes
1-7 with N,N-dimethylaniline affords novel triarylmethanes 8-14 in good yield. The triarylmethane 8 is irradiated at 325 nm for 1 hr under different solvent systems and the photoproducts are identified as 15 and 16.

 

 

Ponnusamy Shanmugam* & Luxmi Varma

 

 

 

 

 

 

 

1264

Ammonium chlorochromate adsorbed on silica gel for cleavage of carbon-nitrogen double bonds under non-aqueous condition

Oximes, p-nitrophenylhydrazones, 4-phenylsemicarba-zones and semicarbazones are converted to their corresponding carbonyl compounds in good yields using ammonium chlorochromate adsorbed on silica gel (ACC/SiO2) under non-aqueous condition.

 

 

Gui-Sheng Zhang* & Bing Chai

 

 

 

 

 

 

 

1267

Semiempirical molecular orbital calculations of configurational properties of dihalogenated sulfur diimides

 

 

 

Mansour Zahedi*, Ahmad Shaabani &
Mohammad Reza Shariat Zadeh

 

 

 

 

 

 

 

1270

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

A series of new 2-(1,8-naphthyridin-2-one-3-yl)[1,3,4]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 acid hydrazide 1 and subjected to antibacterial activity studies.

 

 

K Mogilaiah*, H Ramesh Babu &
R Babu Rao

 

 

 

 

 

 

 

 

1275

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

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

 

 

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

 

 

 

 

 

 

 

 

 

1279

Aminothiazoles: Part 1¾Syntheses and pharma-cological evaluation of 4-[isobutylphenyl]-2-substituted-aminothiazoles

 

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

p-Isobutyl phenacyl chloride has been prepared by the reaction of chloroacetyl chloride on isobutyl benzene. It is condensed with thiourea and its derivatives to get the title compounds.

 

 

 

 

 

 

 

 

 

1282

A new sterol from Holarrhena antidysenterica seeds

A new sterol, named holarrhenosterol, isolated from the seeds of Holarrhena antidysenterica  along with b-sitosterol, has been characterized as 5a-stigmasta-9(11), 20(21)-dien-3b-ol on the basis of spectral data analysis and chemical means.

 

 

 

 

Ajay Kumar & Mohammed Ali*

 

 

 

 

 

 

 

 

 

1285

New diterpenoid alkaloids from Delphinium souliei Franch

Two new diterpernoid alkaloids have been isolated from Delphinium souliei Franch, and their structures established as Souline E and F on the basis of spectral evidences.

 

Souline E                               Souline F

 

Lan He, Yuan Jiang Pan & Yao Zu Chen

 

 

 

 

 

 

 

1287

Arabinoxylan from Cryptocarya wightiana Bark

 

 

 

 

 

 

Gudipati Muralikrishna &
 Rudrapatnam N Tharanathan*

A homogeneous arabinoxylan (Ara-Xyl in 1.05:1 ratio) has been obtained from the major water soluble fraction of Crypotocarya wightiana bark gum by employing gel filtration on Sephacryl S-400 and SE-HPLC techniques. Methylation of the pure polysaccharide followed by GLC-MS analysis reveals a highly substituted 1,4-linked xylan backbone.

 

 

 

 

 

 

Authors for correspondence are indicated by (*)

 

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