Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 40B

NUMBER 9

SEPTEMBER 2001

CONTENTS

Advances in Contemporary Research

 

 

 

763

Catalytic metathesis reaction in organic synthesis

 

 

Sambasivarao Kotha* &

Nampally Sreenivasachary

Catalytic metathesis reaction in organic synthesis has been reviewed.

 

 

 

 

Papers

 

 

 

 
781

Synthesis and photochemistry of 2,2-di-tert-butyl-6-(4,4-di-tert-butylbuta-1,3-dienyl)-2H-pyran

 

 

 

 

 

Pinar Kilickiran, Sethuraman Sankararaman

& Henning Hopf*

 

 

 

 

 

 

 

786

Crystal and molecular structure of N-(3¢,4¢,5¢-trimethoxybenzylidine)-3-chloro-4-fluoroaniline

 

 

 

 

K V Arjuna Gowda, M M Kokila, Puttaraja,

M V Kulkarni, J Shashidhara Prasad &

N C Shivaprakash*

Crystal structure of the title compound has been determined by X-ray methods.

 

 

 

 

 

 

 

                                                Ag+ & Et3N,

X-NH-CHR-COCHN2                                                 X-NH-CHR-CH2-COO-C6H4-NO2(o)

                                                o-nitrophenol

X  = Fmoc, Boc or Z gorup

 
790

Convenient and simple homologation of Na-urethane protected a-amino acids to their b-homologues with concomitant o-nitrophenyl-esters formation

 

 

 

 

 

 

 

 

Kuppanna Ananda, Hosahudya N Gopi &

Vommina V Suresh Babu*

The Wolff rearrangement of Na protected a-aminodiazoketones in presence of o-nitrophenol catalyzed by silver acetate at low temperature is described. Thus the homologation of Boc-/Z-/Fmoc-a-amino acids to b-amino acids with concomitant formation of the corresponding o-nitrophenyl esters has been achieved by this method.

 

 

 

 

 

 

796

Synthesis of C7-C16-alkyl glycosides: Part 4¾Synthesis of alkyl d-glucopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S Konstantinović,*, J Predojević,

B Mojsilović, B Dimitrijević & G Milošević

The Lewis acid catalyzed glycosylation reaction of b-peracetylated sugar derivative (glucose) with fatty alkanols is used in a synthesis of C7-C16-alkyl glucopyranosides. The process occurs under the influence of tin(IV) chloride.

 

a) Ac2O, NaOAc    b) ROH(3), SnCl4    c) NaOMe, MeOH

 

 

 

 

 

 

802

Synthesis of C3-C9-alkenyl 2,3-unsaturated glucosides from glucose and some alkenols

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S Konstantinović*, J Predojević, S Gojković,

Z Ratković, B Dimitrijević & B Mojsilović

C3-C9-Alkenyl 2,3-unsaturated glucosides have been synthesized from glucose and C3-C9-alkenols by using Ferrier reaction with BF3.Et2O as Lewis acid catalyst in key step.

 

 

 

 

 

 

 

806

Oxidation chemistry of 4-hydroxy and 5-hydroxyindoles in micellar medium

 

 

 

 

 

 

 

 

Rajendra N Goyal*, Neeraj Kumar &

Bhanu P Srivastava

Oxidation of 4- and 5-hydroxyindoles has been studied at a pyrolytic graphite electrode and a comparison of behaviours in aqueous and micellar media is reported.

 

 

 

 

 

 

813

New antihistaminic agents: Part 6¾Synthesis and H1-antihistaminic evaluation of 3-[(N,N-dialkylamino)alkyl]-6-halo-2-phenyl-3,4-dihydroquinazolin-4(3H)-ones

 

 

 

 

S Dev Singh, M Bhagavan Raju,

Rajesh H Bahekar, K S Rajan &

A Raghu Ram Rao*

Synthesis of some 3-[N,N-dialkylamino)alkyl]-6-halo-2-phenyl-3,4-dihydroquinazolin-4(3H)-ones 3 is described. The antihistaminic activity of the compounds is reported uisng in vitro and in vivo animal models.

 

 

 

 

 

 

 
817

Synthesis and antimicrobial activity of N-(substituted phenyl)-N¢[1,2,3,4-tetrahydro-2-oxido-1,3,2-benzodiazaphosphorine-2-yl]ureas

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

L Nagaprasada Rao,

C Devendranath Reddy* & B Sankar Reddy

N-(Substituted phenyl)-N ¢-[1,2,3,4-tetrahydro-2-oxido-1,3,2-benzodiazaphosphorine-2-yl]ureas 5 which are substituted ureas of the type RR¢P(O)NHC(O)NR¢¢R¢¢¢ have been synthesized from reactions of 2-amino-benzylamine 2 with chlorides of arylcarbamidophosphoric acids 4 in the presence of triethylamine at 40-45°C. Their antimicrobial activity is reported.

 

 

 

 

 

 

 

 
822

Synthesis and antimicrobial activity of 2-substituted-2,3-dihydro-1H-naphtho-[1,8-de]-1,3,2-diazaphosphorine 2-oxides/sulfides

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

M Venugopal, C Devendranath Reddy* &

M Bavaji

Several 2-alkylcarbamato/thiocarbamato/arylcarbamido/ trichloromethyl/bis (2-chloroethyl)amino/chloroethoxy/ aryloxy-2, 3-dihydro-1H-naphtho-[1,8-de]-1, 3, 2-diaza­phos­­phorine 2-oxides/sulfides (4 and 6) are synthesized by reacting equimolar quantities of 1,8-diamino-naphthalene 1 with various dichlorophosphinyl carbamates/thiocrbamates/arylcarbamides 3a-l, trichlromethyl-phosphonic dichloride 5a, bis(2-chloroethyl)phos-phoramidic dichloride 5b, O-2-chloroethyl phosphoryl chloride 5c and arylphosphorothioic dichlorides 5d-e in the presence of triethylamine at 45-65°C. Their IR, 1H, 13C, 31P NMR and mass spectral data are discussed. All these compounds are found to have significant antifungal and antibacterial activity.

 

 

 

 

 

 

828

Synthesis, antimicrobial and antituberculosis activities of N-bridged heterocycles

 

 

 

 

 

 

 

 

U V Laddi, M B Talawar, S R Desai,

R S Bennur & S C Bennur*

Synthesis and antimicrobial and antituberculosis activities of N-bridged heterocycles derived from triazoles
1a-d is described.

 

 

 

 

Notes

 

 

 

 
834

Synthesis of substituted 2-iminothiopyrans from aryl ethylidene malononitriles

 

 

 

 

 

 

 

 

 

 

 

Reichel Samuel & C V Asokan*

The reaction of arylethylidene malononitriles 1 with dimethyl trithiocarbonate in the presence of sodium hydride in benzene gives 4-aryl-2-imino-6-methylthio-2H-thiopyran-3-crbonitriles 5 in good yields.

 

 

 

 

 

 

 

 
837

Microwave assisted synthesis of 1,8-naphthyridines

 

 

 

 

 

 

 

K Mogilaiah*, N Vasudeva Reddy &

R Babu Rao

An efficient and rapid method for the synthesis of 1,8-naphthyridines 3 under microwave irradiation is described.

 

 

 

 

 

 

 

 

 
839

A convenient and simple transformation of acylhydrazones to diacylhydrazines employing m-chloroperbenzoic acid under solid state conditions

 

 

 

 

 

 

 

 

 

K Mogilaiah* & P Raghotham Reddy

A simple and efficient method for the oxidation of acylhydrazones 2 to N,N¢-diacylhydrazines 4 using m-chloroperbenzoic acid (m-CPBA) in the solid state has been described.

 

 

 

 

 

 

 
842

New versatile halogenating reagents for hydroxy groups

 

 

 

 

 

 

 

 

 

 

Sanjay Kumar, Krishna K Dubey,

Yashveer Singh & Krishna Misra*

Synthesis of some new halogenating reagent, viz. ATPB/ATPC is described. Halogenation of alcohols and 3¢ & 5¢-OH function of nucleosides is reported using these reagents.

 

 

 

 

 

 

 

846

The behaviour of pyrazole and isoxazole derivatives under electron impact conditions

 

 

 

 

 

 

 

 

 

 

V Padmavathi*, R P Sumathi, A Padmaja &

D Bhaskar Reddy

The mass spectral behaviour of some pyrazole and isoxazole derivatives has been studied under electron impact conditions.

 

 

 

 

 

 

 

 

850

Naphthalene derivatives as fluorescent probe

 

 

 

 

 

 

Tarasankar Pal*, Tarun K Ghosh &

Anjali Pal

Naphthalene derivatives as fluorescent probes in anionic micelle have been examined on the basis of fluorescence enhancement.

 

 

 

 

 

 

 

 
854

Synthesis and antifungal activity of w-(1-aryl-5-methyl-1,2,3-triazole-4-carboxyl)-w-(1H-1,2,4-triazol-1-yl)acetophenones

 

 

 

 

 

 

 

 

 

 

 

Chang-Hu Chu, Xiao-Wen Sun,

Zi-Yi Zhang*, Zhi-Chun Li & Ren-An Liao

w-(1-Aryl-5-methyl-1, 2, 3-triazole-4-crboxyl)-w-(1H)-1, 2,4-triazol-1-yl)acetophenones 3a-j have been synthesized. The preliminary biological test results show that the representative compounds exhibit mild antifungal activities.

 

 

 

 

 

857

Hydroquinone O-b-d-xylopyranoside from Centipeda minima

 

 

 

 

 

 

 

 

 

 

Rashmi Sanghi*, Punita Srivastava &

J Singh

A new glycoside, 2-isopropyl-5-methyl-p-hydroquinone-4-O-b-d-xylopyranoside together with sitosterol and a stilbene derivative have been isolated from the whole plant of Centipeda minima.

 

 

 

 

 

 

 

 
860

Two new anthraquinone glycosides from the leaves of Cassia occidentalis

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Deepa Chauhan*, J S Chauhan* &

J Singh*

 

 

 

 

 

 

 

864

Justicia lignans: Part 8¾Lignans from Justicia orbiculata Wall.

 

 

 

 

 

Gadamsetty V Ramesh Babu,

Jakka Kavitha &

Gottumukkala V Subbaraju*

Aryloxyfurofurans, 1 and 2 have been isolated and characterized. 13C NMR data are assigned.

1 R = R¢ 3,4-Methylenedioxyphenyloxy

2 R = 3,4-Methylenedioxyphenyl

  R¢ = 3,4-Methylenedioxyphenyloxy

 

 

 

 

 

 

867

New sesquiterpenoid from soft coral Sinularia dissecta

 

 

 

 

 

 

 

P Ramesh, V Ravikanth & Y Venkateswarlu*

New sesquiterpenoid 15-hydroxy-D9-africanene 1 has been isolated from the soft coral Sinularia dissecta and its structure elucidated based on spectral analysis.

 

 

 

 

 

 

Authors for correspondence are indicated by (*)

 

 

 

 

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