CONTENTS

INDIAN J CHEM, 54B (4)2015

499

Website address: www.niscair.res.in; http://nopr.niscair.res.in

Indian Journal of Chemistry

Sect. B: Organic Chemistry including Medicinal Chemistry

VOL. 54B NUMBER 4 April 2015

CONTENTS

Papers

505 Synthesis of conformationally constrained α-amino

acid derivatives containing bicyclo[2.2.2] unit via the

Diels-Alder and Suzuki-Miyaura cross-coupling

reactions as key steps

A simple route to synthesize conformationally constrained α-amino

acid (AAA) derivatives containing bicyclo[2.2.2]octane ring-system

has been devised. Diels-Alder reaction has been chosen to assemble

highly constrained AAA derivatives and further expanded the scope

of the methodology by Suzuki-Miyaura cross-coupling reaction

with various boronic acids.

Sambasivarao Kotha*, Milind Meshram & Gopinathan Muthusamy

Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400 076, India

514 Synthesis and fluorescence studies on menthol-

coumarin conjugates

A three-step protocol for synthesis of alcohol containing aliphatic

natural products and coumarins has been described. The Blaise

reaction of converting the nitrile to β-keto esters formed key-step in

this protocol. The absorption and fluorescence emission studies of

menthol-coumarin conjugates revealed that menthol substitution has

little influence on the absorption or emission characteristic of the

chromophore. However, substitution of C(6)H or C(6)OMe of the

coumarin with NEt2 has dramatic influence on both absorption and

emission of the conjugate. Solvatochromic studies and analysis of

Stoke shift data show that the menthol-coumarin conjugate with

C(6)NEt2 stabilizes in dipolar push-pull structure in ground and

excited states.

H Surya Prakash Rao* & Avinash Desai

Department of Chemistry Pondicherry University, Pondicherry 605 014 India

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INDIAN J CHEM, 54B (4)2015

500

525 Synthesis and screening of sugar triazolidines for

antimicrobial activity

Several new 1-sugar-3-cyanoamidino carbamides have been

synthesized by the interaction of sugar isocyanates with

dicyandiamide in acetone medium. Furthermore several novel 1-

cyano-2-sugar-3-one-5-imino-1,2,4-triazolidines have also been

synthesized by the oxidative cyclisation of 1-sugar-3-cyanoamidino

carbamides.

O

BzO

BzOOBz

OBzOAcO

AcOOAc

OAc

O

AcO

AcOOAc

OAc

OO

AcOOAc

OAc O

BzO

BzOOBz

OBz

OO

BzO

OBz

OBz

NH2 C

NH

NH CNNCO

NHC

NH

O

C

NH

NHCN

N N CN

CO

C

NHN

H

[O]

N N CN

C

O

CNH

N

H

CO

C

NHN

H

N N CN

OOBz

OOBzO

OBz

OBz

N N CN

CO

CNHN

H

BzO

BzOOBz

O

OAc

AcOOAc

OAc

OO

AcOOAc

OAc

N N CN

CO

CNHN

H

N N CN

CO

CNHN

H

N N CN

CO

CNHN

H

Sugar +

Acetone Reflux, 3 hr 30 min

1(a-f) 2

3(a-f)

Br2/CHCl3

4(a-f)

Sugar

4a 4b

4c4d

4e4f

Renu B Ghayalkar* & Shirish P Deshmukh

P. G. Department of Chemistry, Shri Shivaji College of Arts, Commerce and Science, Akola 444 003, India

CONTENTS

INDIAN J CHEM, 54B (4)2015

501

531 Synthesis of N-alkylated-2-(1,3-diphenyl-1H-pyrazol-

4-ylsulfanyl)-1H-benzimidazoles by Vilsmeir-Haack

reaction and by condensation with DMF-DMA

N-Alkylated-2-(1,3-diphenyl-1H-pyrazol-4-ylsulfanyl)- 1H-benzimi-

dazole 7a-d have been prepared by four different methods using

three distinct stages in each method from 2-(1H-benzimidazol-2-

ylsulfanyl)-1-phenylethanone 3.

S Srinivas Rao*, Putluru Mahesh, Ch Venkata Ramana Reddy & P K Dubey

Department of Chemistry, Jawaharlal Nehru Technological University, Hyderabad College of Engineering, Kukatpally,

Hyderabad 500 085, India

538 Comparative studies of synthesis of symmetric 2,6-di-

(benzofuran-2-yl)-4-phenyl-pyridine derivatives via

pyrylium tetrafluoroborate salt and 1, 5-dione

derivatives

Synthesis of symmetric 2,6-di(benzofuran-2-yl)-4-phenyl-pyridine

derivatives 4a-h has been reported by two methods. Method A

follows nucleophilic substitution reaction of 2,6-di (benzofuran-2-

yl)-4-phenyl-pyrilium tetrafluoroborate salt derivatives 3a-h with

ammonium acetate in ether at room temperature. Method B follows

cyclisation reaction of 1,5-di (benzofuran-2-yl)-3-(4-substituted-

aryl)-pentane-1,5-dione derivatives 2a-h with ammonium acetate in

acetic acid under reflux. It has been found that method B proceeds

under mild reaction condition with short reaction time and high

yield when compared to method A. The structures of the newly

synthesized compounds are characterized by spectral studies.

O

CH3

O

R

NO O

R1

R R

O+O O

R1

R R

BF4

-

Method A

Method B

OO O

R1

R R

O

D B Aruna Kumar*, Nivedita R Desai, G Krishnaswamy, S Sreenivasa & K M Mahadevan

Prof C N Rao Centre for Advance Materials, Tumkur University, Tumkur 572 103, India

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INDIAN J CHEM, 54B (4)2015

502

545 Multicomponent synthesis of highly functionalized

piperidines using sulfamic acid as a heterogeneous

and cost effective catalyst

A one pot multicomponent synthesis of some new densely

functionalized piperidines derivatives using sulfamic acid as an

efficient and cost effective catalyst is described.

Dayanand Patil, Dattatray Chandam, Abhijeet Mulik, Prasad Patil, Suryabala Jagdale & Madhukar Deshmukh*

Heterocyclic Laboratory, Department of Chemistry, Shivaji University, Kolhapur 416 004, India

551 Synthesis of novel Schiff bases and evaluation of

their antimicrobial activities

The novel Schiff bases 4a-f were synthesised from the

corresponding dihydropyrimidinones 1a,b by converting the

dihydropyrimidinones to 1,3,4-thiadiazol-2-amine, 3a,b via

hydrazinecarbothioamide, 2a,b. 1,3,4-Thiadiazol-2-amine, on

condensation with various selected aromatic aldehydes furnished

Schiff bases, 4a-f.

NH

NHC

H3C

R1

O

O

1(a-b)

CH3C

O

H

H

NH

NH

R1

ON

N

H

O

H3CH

S

NH22(a-b)

NH

NH

H3C

R1

O

NN

SH2N

3(a-b)

NH

NH

H3C

R1

O

NN

SN

CR2

H

4 ( a-f )

4a, R1 = R2 = C6H5. b, R1 = C6H5 , R2 = 4-CH3.C6H4.

c, R1 = C6H5 , R2 = 3-OH.C6H4. d, R1 =4-CH3 C6H4 , R

2 = C6H5.

e, R1 = R2 = 4-CH3 C6H4. f, R1 = 4-CH3 C6H4 , R2 = 3-OH. C6H4

C A M A Huq* & S Fouzia

P G and Research Department of Chemistry, The New College, Chennai 600 014, India

CONTENTS

INDIAN J CHEM, 54B (4)2015

503

556 Synthesis and biological screening of 1,2,4-triazole

derivatives

A series of 2-((arylamino)methyl)-5-(3-methoxyphenyl)-1-phenyl-

1H-1,2,4-triazole-3-thione derivatives have been synthesized and

characterized by FT-IR, NMR, mass spectral and elemental

analysis. Compounds MM4a-m have been evaluated for their in vitro

antibacterial, antifungal and antitubercular activity. Of all the

compounds MM4d, MM4e, MM4j and MM4k show good

antibacterial activity and MM4a, MM4d, MM4e and MM4j

compounds have been found to possess good antitubercular activity.

Dinesh R Godhani*, Anand A Jogel, Anil M Sanghania & Jignasu P Mehta

Department of Chemistry (DST-FIST & UGC NON-SAP Department), Mahatma Gandhi Campus, Maharaja

Krishnakumarsinhji Bhavnagar University, Bhavnagar 364 002, India

Notes

565 Synthesis and antimicrobial activity of new S-alkyl

isothiosemicarbazone derivatives of pyrimidine

A series of S-alkyl isothiosemicarbazone derivatives of 2,4,6-

trisubstituted pyrimidine are synthesized.

N

N

1

H3C

CH3

EtO2C

N

CH3

F

N

N

H3C

CH3

N

F

SO2CH3

CH3

NNH2N

SR

3 a-i

SO2CH3

Hemant N Raundal, Rahul P Jadhav, Amar A Patil, Pravin C Mhaske & Vivek D Bobade*

Department of Chemistry, H.P.T. Arts and R.Y.K. Science College, Nashik 422 005, India

CONTENTS

INDIAN J CHEM, 54B (4)2015

504

570 Sulfur-sulfur bond formation through cyclo

condensation: Synthesis of some N-glucosylated

dithiadiazines

Chloroform,Reflux, 3h

RNH

C

S

NH

H2N

OAcO

AcOO

OAc

N

5

Controlchlorination

4

3Ac

OAcO

AcOO

OAc

AcN C S

OAcO

AcOO

OAc

AcN C

Pb(SCN)2,Xylene,

reflux, 3hO

AcOAcO

BrO

OAc

Ac

OAcO

AcOO

OAc

AcNH

S

NHNH2

ChloroformReflux, 3h

R N C S

Cl

NH2NH2

chloroform

RT, 30min

1 2 6

7

S S

NHHN

N

R

Cl

Cl

S Cl

A G Ulhe, S A Chavan & B N Berad*

Department of Chemistry, Mahatma Jyotiba Phule Educational Campus, Rashtrasant Tukadoji Maharaj Nagpur University,

Nagpur 440 033, India

Authors for correspondence are indicated by (*)