463
Indian Journal of Chemistry
Sect. B: Organic Chemistry including Medicinal Chemistry
VOL. 46B
NUMBER 3
MARCH 2007
CONTENTS
Papers
471
HPAEC and MALDI-TOF-MS analysis of oligosaccharides generated from sesame meal by enzymatic hydrolysis
IPC: Int.Cl.8 C07C
Generation of xyloglucan oligosaccharides 1 through
6 from Sesamum indicum meal by enzyme hydrolysis
and their characterisation by sugar compositional and
linkage analysis, HPEAE-PAD-chromatography and
MALDI-TOF-mass spectrometry has been carried out.
Kaushik Chattopadhyay, Partha Ghosh, Pradyot
Ghosal & Bimalendu Ray*
INDIAN J CHEM, 46B (3) 2007
CONTENTS
464
478
Prediction of acidity constant for substituted
acetic acids in water using artificial neural
networks
IPC: Int.Cl.8 C07C
Linear and non-linear quantitative structure-activity
relationships have been successfully developed for the
modeling and prediction acidity constant (pKa) of 87
substituted acetic acids with diverse chemical structures.
6
ANNtrain
5
ANNvalid
ANNpred
Linear (ANNpred)
Calculated
4
3
2
1
0
0
1
2
3
4
5
6
Experimental
Aziz Habibi-Yangjeh* &
Mohammad Danandeh-Jenagharad
488
Synthesis of 1-alkyl/aralkyl-2-(1-arylsul fonylalkyl)benzimidazoles under PTC conditions
IPC: Int.Cl.8 C07D
+
- Na
H
N
1
N
(i)
R
C Cl
H
A
r-SO 2
1
RO
2-(α-Chloroalkyl)benzimidazoles 1 on reaction with
arylsulphinate sodium salt 2 in CH3CN under PTC
conditions, give 3 which on alkylation yields 1alkyl/aralkyl 2-(α-arylsulfonylalkyl)benzimidazoles 4.
Alternatively, 4 can also be prepared by the reaction
of 2 with 1-alkyl/aralkyl-2-(α-chloroalkyl)benzimidazole 5 in CH3CN using PTC conditions.
/ TEBAC
1
or
-OR
-SO 2
/ CH
R 1-
3 CN
R1
N
X
)
(ii
(i) R
1
O(ii
SO
)
1 -X
2 -O
R
ArR 1 or
CN
SO 3
H
C
2 Na +
/ TEBAC /
4
N
R
C
H
SO2 Ar
P K Dubey*, P V V Prasada Reddy & K Srinivas
INDIAN J CHEM, 46B (3) 2007
CONTENTS
492
Three new compounds 1-3 along with β-sitosterol and
its glucoside, stigmasterol, d-mannitol, ursolic acid
and oleanolic acid have been isolated from aerial parts
of Evolvulus nummularius (Convolvulaceae).
Chemical constituents of Evolvulus nummularius
IPC: Int.Cl.8 C07C
R' O
465
H
H O
C
C C OR
1 R΄= stearoyl, R= stigmasteryl
H
C C C OO (CH2
H
HO
COOH
)
15
2
HOOC
H
H
HO
H
3s
Biswanath Dinda*, Biplab Ghosh, Shiho Arima,
Nariko Sato & Yoshihiro Harigaya
499
Novel one-pot synthesis of 1,3-dithiins and 1,3-thiazines
under microwave irradiation
IPC: Int.Cl.8 C07D
R'.CH=O,
R''.NH.CS.SH,
NaCl, MWI
S
S
CH2
N
S
C
S
2
S
N
2
O
H
S
S
N
CH2
H
H
R'
R'.CH=O,
R''.NH.CS.SH,
NaCl, MWI
S
CH2
H
Microwave induced synthesis of 1,3-dithiins and 1,3thiazines involving Knoevenagel condensation
followed by Michael addition under solvent-free
conditions in one-pot is reported. The reaction is
catalyzed by cheap and easily available NaCl.
OH
H
R''
N
C
S
R'' N
2
R'
S
3a-j
1
4a-j
Ibadur R Siddiqui* & Pravin K Singh
INDIAN J CHEM, 46B (3) 2007
CONTENTS
466
505
Synthesis of CL-20: By oxidative debenzylation
with cerium(IV) ammonium nitrate (CAN)
IPC: Int.Cl.8 C07D
CH3 CO
CH3 CO
C6 H5 CH2
N
N
CH3 CO
N COCH3
N
COCH3
N
N
A simple debenzylation approach has been discussed
for the synthesis of hexanitrohexaazaisowurtzitane
(HNIW or CL-20) one of the most powerful high
explosives of today with cerium ammonium (IV)
nitrate.
CAN
CH3 CO
N
N COCH3
N
N
COCH3
Acetylation
CH3 CO
CH2 C6 H5
N
N
HAIW
COCH3
TADBIW
Nitration
CAN
Nitration
O2 N
O2 N
O2 N
N
N NO2
N
N
NO2
N
N
NO2
CL-20
G M Gore, R Sivabalan*, U R Nair, A Saikia,
S Venugopalan & B R Gandhe
509
-Selectivities of trans-2-heterobicyclo[4.4.0]decan5-ones in reductions with NaBH4 and Na(CN)BH3
IPC: Int.Cl.8 C07D
H
H
O
X
The nheteroatom→*# interaction hypothesis to explain
the relative reaction rates and the axial selectivities of
nucleophilic additions to 2-heterobicyclo[4.4.0]decan-5-ones in relation to the corresponding carbaanalog does not find experimental as well as theoretical support. The selectivity is rather dependent on the
differential electron-withdrawing abilities of the heteroatoms that translate further into differential
vicinal→*C=O interactions in the ground states of the
molecules. The heightened axial selectivity of the azaspecies is probably due to hydrogen bonding of nitrogen with the solvent that enhances its electron withdrawing ability further.
H
H
OH
X
H
H
OH
X
Rengarajan Balamurugan,
Vardhineedi Sriramurthy & Veejendra K Yadav*
INDIAN J CHEM, 46B (3) 2007
CONTENTS
516
467
Two new triterpene glycosides have been reported
from Oryza sativa and structure elucidated by
spectroscopic methods.
Orizalanasteroloide A and B from rice hulls of
Oryza sativa
IPC: Int.Cl.7 C07C
21
21
CO
H
20
17
OHC
19
11
1
6'
o
OH
HO 3'
OH
3
5'
1'
2'
18
24
23
25
H
13
19
O
29
28
H
11
1
26
HO
H
HO
30
20
17
OHC
27
14
2
HO
4'
H
O
22
22
18
CO
H
O
6''
6
4''
OH
3
O
5'
o
OH
30
6
29
1'
26
H
14
2
6'
13
27
25
H
28
H
2
o O 3'
OH
OH
1''
OH
OH
4'
H
24
23
3''
2'
OH
Ill-Min Chung, Mohd Ali & Ateeque Ahmad*
Notes
523
Synthesis and spectrum of new Schiff bases as
polydentate ligands and potential antibacterial
reagents
IPC: Int.Cl.7 C07D
Eight novel linear polydentate Schiff base ligands,
N,N′-bis(R-iminoethyl)-2,6-pyridinedicarboxylic
diamide IIa-g, have been synthesized. Microcalorimetric test of the inhibitory capacities of these
compounds on E. coli and S. aureus show that they
have antibacterial activity to different extent.
Li-Hua Cai, Pei-Zhi Hu *, Xiao-Lan Du,
Li-Xia Zhang & Yi Liu
529
Lewis acid catalyzed amino-Claisen rearrangement: A facile one pot synthesis of 2-allylarylamines from N-allylarylamines
Boron trifluoride-diethyl ether complex efficiently
catalyzes a variety of amino-Claisen rearrangement of
N-allylarylamines 1a-g to afford 2-allylarylamines
2a-g in moderate to good yields.
IPC: Int.Cl.8 C07C
R
N
H
BF3.OEt2, sulfolane
160-200C, 2h
1a-g
R
NH2
2a-g
Seema Jain, Neelesh Pandey & D Kishore*
INDIAN J CHEM, 46B (3) 2007
CONTENTS
468
532
Synthesis of pyrazole and isoxazole in triethanolamine medium
IPC: Int.Cl.8 C07D
Br2 in AcOH
OH
C CH CH
R
O
Reaction of 2'-hydroxy chalcone dibromides with
phenyl hydrazine and hydrazine hydrate affords
pyrazoles and with hydroxylamine hydrochloride give
isoxazoles in triethanolamine medium. Similarly
reaction of -diketone with phenyl hydrazine and
hydrazine hydrate in TEA gives pyrazoles in high
yield in shorter time.
R1
OH
C CH CH
R
1a-l
R1
Br
O Br
2a-l
NH2OH.HCl
R2NHNH2
TEA
TEA
R2
OH
N
O
OH
R1
R
R
N
N
R1
4a-l
5a-f
OH
R
R1
C CH2 C
O
O
3b-e
Nitin N Agrawal* & P A Soni
535
Enamination of 1,3-dicarbonyl
catalyzed by tin tetrachloride
compounds
IPC: Int.Cl.8 C07C
O
Tin tetrachloride has been found to be an extremely
efficient catalyst for the enamination of 1,3dicarbonyl compounds under solvent-free conditions
at room temperature.
O
R1
R3
2
+ H2NR4 SnCl4·5H2O
R1
r. t.
R
O
HN
R4
R3
R2
Zhan-Hui Zhang*, Zi-Chuan Ma & Li-Ping Mo
INDIAN J CHEM, 46B (3) 2007
CONTENTS
540
469
Hydrolytic cleavage of 2-acetylbezofuran hydrazone
under acidic condition with aromatic aldehyde is
described.
Reaction of 2-acetylbenzofuranhydrazone with
aromatic aldehydes: Formation of aldzaines and
regeneration of 2-acetylbenzofuran
IPC: Int.Cl.8 C07D
O O
CH3
NH2NH2.H2O
N
NH2
O CH
3
2
HCl / C2H5OH
1
2.R-CHO
R-CHO
HCl / C2H5OH
O O
1
R
CH3 +
C2H5OH
R-CHO
N
N R
3a-f
N
N
O CH
3
4a-f
HCl / C2H5OH
R
Ravi K Ujjinamatada* &
Yankangouda S Agasimundin
544
Synthesis and bioactivity study of 2,5-bismercapto-1,3,4-thiadiazole heterocyclic derivatives
A series of acylhydrazone compounds 3 and acylthiosemicarbazides 4 and some heterocyclic derivatives 5
containing thiadiazole rings have been synthesized
conveniently in high yields. The bioassay result indicates that some compounds have relatively low antibacterial activity and bioactivity for improving plant
growth.
IPC: Int.Cl.8 C07D
N
O
N
H2NNH C H2C S
O
S CH2 C NHNH2
S
2
O
Ar C NHN C H2C S
H
N
S CH2
3
N
O
CHN CHNHN CH2CS
R
O
S
O
SCH2C NHNHC NHC
S
R
4
O
N
N
N
N
S
N
N
S CH2
H2C S
CHN
R
S
O
C NHN C Ar
H
N
O
S
N
S
S
O
NHC
R
5
Man-Lin Li, You-Ming Zhang & Tai-Bao Wei*
INDIAN J CHEM, 46B (3) 2007
CONTENTS
470
550
Several Aryl-N-(5-{4-[2-(2-chlorophenyl)-4-oxo(3hydroquinazolin-3-yl)]phenyl}
(1,3,4,thiadiazol-2yl))amides 4a-l have been prepared and tested for
their antibacterial and antifungal activities.
Synthesis and characterization of new quinazolines as potential antimicrobial agents
IPC: Int.Cl.8 C07D
O
S
N
N
N N
R
NH
O
Ar
4
R= 2-Chlorophenyl, Ar = different aryl groups
N C Desai*, P N Shihora & D L Moradia
Authors for correspondence are indicated by (*)
IPC: International Patent Classification
Int.Cl8.: International Classification, 8th Edition, 2006
INDIAN J CHEM, 46B (3) 2007