Indian Journal of Chemistry

 

Sect. B: Organic Chemistry including Medicinal Chemistry

Total visitors: 1,381  since 10-10-06

 

VOL. 45B

NUMBER 9

SEPTEMBER 2006

CONTENTS

Papers

 

 

 

2059

Stereochemistry of N-acyltetrahydro-1,5-benzodiazepines using NMR spectra, X-ray crystallography and semiempirical MO calculations

 

IPC: Int.Cl.8 C07D

The preferred conformations of N-acyl derivatives of 2,2,4-trimethyl-1H-tetrahydro-1,5-benzodiazepines 6-9 have been studied using NMR spectral techniques. In the case of N1, N5-diformyl derivative 9, there is an equilibrium between the boat BE and chair CE conformations. The X-ray crystal structure 7 also shows the boat conformation BE with the exo orientation of the N-CO group. The semiempirical molecular orbital calculations (AM1 and PM3) support the conformational preferences derived from the NMR results.

 

 

 

 

S Ponnuswamy*, R Murugadoss, R Jeyaraman,
A Thiruvalluvar  & V Parthasarathy

 

 

 

 

 

 

 

2071

Synthesis, characterization and biological studies on some triazolothiadiazines and triazolothiadiazoles containing
6-chloropyridin-3-yl-methyl moiety

 

IPC: Int.Cl.8 C07D

 

The synthesis, antibacterial  and insecticidal activities of 4-amino-5-(6-chloropyridin-3-yl methyl)-4H-1,2,4-triazole-3-thiol, 3-(6-chloropyridin-3-yl methyl)-6-(4-substituted phenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines and (6-chloro-pyridin-3-yl methyl)-6-(4-substituted phenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles are described.

 

 

 

 

B Shivarama Holla*, C S Prasanna, Boja Poojary, K S Rao & K Shridhara

 

 

 

 

 

 

 

2077

A facile synthesis of N-phenyl-6-hydroxy-3-bromo-4-arylazo quinoline under phase transfer catalytic conditions and studies on their antimicrobial activities

 

IPC: Int.Cl.8 C07D

Interaction of N-phenyl-2,5-dihydroxy-3-arylazo indoles with dibromocarbene under phase transfer catalysis conditions at 50-60oC and 600 r.p.m. results in a cycloaddition of the in situ generated carbene to the C=C bond followed by skeletal rearrangement in the indole frame work to yield quinoline nuclei. The structure of the compounds are established on the basis of their elemental, IR and 1H NMR and 13C NMR data. All the synthesized compounds have been evaluated for their in vitro growth inhibitory activity. 

 

 

 

 

Pratibha Sharma*, Ashok Kumar & Priti Pandey

 

 

 

 

 

 

 

2083

Study of [1,3] sigmatropic hydrogen migration in uracil, uridine and uridylic acid by AM1 method

 

IPC: Int.Cl.8 C07D

The geometry and electronic structures of uracil, uridine and uridylic acid involving  [1,3] sigmatropic hydrogen migration in the formation of tautomers have been fully optimized and evaluated by semi-empirical molecular orbital AM1 method. In this connection, the heats of formation (DHf°), dipole moments (m), full atomic charges, and energies of frontier molecular orbitals (EHOMO and ELUMO) have been calculated and discussed. All tautomers exist with in the energy of 20.569 kcal/mol. Furthermore, dipole moment and atomic charges of all tautomers indicated that the dipole-dipole interactions play a vital role during the synthesis of proteins and enzymes.

 

 

Bojja Rajeshwar Rao

 

 

 

 

 

 

2091

Synthesis of new 4-aryl-isoxazolo[5,4-d]pyrimidin-6-one(thione) and 4-aryl-pyrazolo[3,4-d]-pyrimidin-6-one derivatives of potential antihypertensive activity

 

IPC: Int.Cl.8 C07D

Hydroxyl amine reacts with 5-acetyl-4-aryl-tetrahydropyrimidines to give isoxazolo-pyrimidines via a Michael-type addition of the hydroxyl proton to the double bond of the pyrimidine ring. An oxygen bridged pyrimidines break at the oxygen atom with formation of isoxazolo derivatives. Hydrazine hydrate reacts similarly with some compounds to give pyrazolo-pyrimidines. 

 

 

 

 

Wageeh S El-Hamouly, Abdel-Momen A El-Khamry* & Eman M H Abbas

 

 

 

 

 

 

 

2099

Synthesis of some substituted azetidinonyl and thiazolidinonyl-1,3,4-thiadiazino[6,5-b]indoles as prospective antimicrobial agents

 

IPC: Int.Cl.8 C07D

Several 2-[(3-chloro-2-substituted phenyl)-4-azetidinon-3-yl]-1,3,4-thiadiazino [6,5-b] indoles and 2-[(2-substituted phenyl)-4-thiazolidinon-3-yl]-1,3,4-thiadiazino[6,5-b]indoles have been synthesized. The structures of the synthesized compounds are characterized by elemental and spectral analysis. These compounds are also  evaluated for their antimicrobial susceptibility test against S.aureus, E.coli, K.pneumoniae, P.vulgaris and A.fumigatus, C.albicans, A. albicans ATCC, C. krusei G03 respectively.

 

 

 

 

Hemant Panwar, R S Verma, V K Srivastava, &
A
shok Kumar*

 

 

 

 

 

 

 

2105

The reaction of tanshinones with diamines

 

IPC: Int.Cl.8 C07D

The reactions of cryptotanshinone and tanshinone IIA with diamines are investigated. Eleven new compounds are obtained. The possible reaction mechanism is proposed.

 

 

 

 

Lin-Kun An, Xian-Zhang Bu, Xiao-Hong Song, Zhi-Shua Huang, Pei-Qing Liu & Lian-Quan Gu*

 

 

 

 

 

 

 

2112

Microwave-mediated synthesis of some novel    heterocycles containing thiazole, oxazole thiazine, oxazine, thiadiazine and  triazolo-thiadiazine moiety

 

IPC: Int.Cl.8 C07D

Synthesis of  five- and six-membered fused ring system such as 2-substituted imino-5,5-dimethyl-2,3,5,6-tetrahydro-4H-benzothiazol-7-one 3, 2-substituted imino-5,5-dimethyl-2,3,5,6-tetrahydro-4H- benzoxazol-7-one 4, 7-substituted-2,2-dimethyl-2,3-dihydro-1H,10H-phenothiazin-4-one 5, 2,2-dimethyl-2,3-dihydro-1H,10H-phenoxazin-4-one 6, Schiff base of 2-hydrazino-6,6-dimethyl-6,7-dihydro-4H,5H-benzo[1,3,4]thiadiazin-8-one 7, Schiff base of 2-amino-6,6-dimethyl-6,7-dihydro-4H,5H-benzo[1,3,4]thiadiazin-8-one  8  and -substituted alkyl-7,7-dimethyl-7,8-dihydro-5H,6H-1,2,4-triazolo[3,4-b][1,3,4]benzothiadiazin-9-one 9, respectively, has been reported by microwave-irradiation as well as by conventional method.  

 

 

 

 

 

Vijay V Dabholkar* & Sushil Kumar J Mishra

 

 

 

 

 

 

 

2118

The synthesis of novel calix[4]arenes containing one and two substituents on the “upper rim”

 

IPC: Int.Cl.8 C07C

Procedures are described for the removal of the p-butyl groups from p-tert-butylcalix[4]arene and the introduction of benzoyl, nitro, amino and acrylamido groups to yield a series of mono- and bis-substituted compounds on the “upper rim” with potential possibility to polymerized with other monomers.

 

 

 

 

 

Li Lei, Lv Ping, Xian chunying & Zheng Limin*

 

 

 

 

 

2123

Synthesis, characterization and biological activity of triazole derivatives of cinitapride

 

IPC:.Int.Cl.8 C07D

New triazole analogues of cinitapride are synthesized by diazotization induced hetero aromatization.  Isomers  resulted from the alkylation of triazole derivative are separated and one of them was synthesized in an unambiguous route. Anti-ulcer activity of all the derivatives is studied in mice.

 

 

 

 

Gudipati Srinivasulu,  Kudavalli Jaya Satyanarayana, Padi Pratap Reddy *, Pragathi Hegde &
Ranjan Chakrabarti

 

 

 

 

 

 

 

2128

Synthesis of [2-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6 carbonyl)-1H-indol-3-yl]acetic acids as potential
COX-2 inhibitors

 

IPC: Int.Cl.8 C07D

 

Michael condensation of ortho tosylamino- acrylic acid esters 5 with chloroacetyl benzoxazinones 6   resulting in the formation of substituted indole acetic acids 1 is reported as potential COX-2 inhibitors.

 

 

 

 

P K Dubey*, T Venkateshwar Kumar, P Reddanna &
K Anilkumar

 

 

 

 

Notes

 

 

 

2133

Advanced polymers for high technology applications

 

IPC: Int.Cl.8 C07D

Synthesis of organic conjugated polymers of pyrrole and formaldehyde is discribed. The reaction is catalyzed by strong acid, weak acids, organic acids and also by Lewis acids. Spectroscopy reveals that the polymers formed are long organic chains that are not only held together by the usual C – C sigma bonds that are found in ordinary polymers, but the electrons.

 

 

 

M N Narule & J S Meshram*

 

 

 

 

 

 

 

2136

Antimicrobial activity of 1-[p{3'-(2'-aryl-4–oxo-1',3'-thiazolyl)} diphenyl]/[-3'-(2'-aryl-4-oxo-1',3'-thiazolyl)]-2-phenyl-4-cyclohexylidene imidazol-5-ones

 

IPC: Int.Cl.8 C07D

Synthesis and antimicrobial activity of 1-[p{3'-(2'-aryl-4–oxo-1',3'-thiazolyl)} diphenyl]/[-3'-(2'-aryl-4-oxo-1',3'-thiazolyl)]-2-phenyl-4-cyclohexylidene imidazol-5-ones have been described.

 

 

 

Abha Bishnoi*, Krishna Srivastava & C K M Tripathi

 

 

 

 

 

 

 

2140

Effect of organized assemblies, Part-III: Micellar catalysed iodo-de-diazoniation reactions

 

IPC: Int.Cl.8 C07C

The yield of iodo-de-diazoniation reaction in micellar phase is found to increase substantially in the presence of cationic surfactant, cetyltrimethylammonium bromide, whereas the reaction does not occur in the presence of nonionic and anionic surfactant systems. The results have been ascribed to the electrostatic attraction between the reactants and the surfactant micelles and  increase in effective concentration of the reactants in micellar phase.

 

 

H P Mishra, S Panigrahi, P K Misra*  & G B Behera

 

 

 

 

 

 

 

2143

Synthesis of methyl-5-[2-arylamino-4-(3-oxo-1,4-enzoxazin-6-yl)thiazole acetates and 7H-[3-aryl-6-(3-oxo-1,4-benzoxazin-6-yl)-s-triazolo[3,4-b][1,3,4]thiadiazin-7-yl]acetates as possible COX-2-inhibitors

 

IPC: Int.Cl.8 C07D

A series of methyl 5-[2-arylamino-4-(3-oxo-[1,4]benzoxazin-6-yl)thiazoleacetates 5a-h and 7H-[3-aryl-6-(3-oxo-[1,4]-benzoxazin-6-yl)-s-triazolo[3,4-b] [1,3,4]thiadiazin-7-yl]-acetates 6a-e have been synthesized and tested for their COX-2 inhibitor activity.

 

 

 

G Jagath Reddy*, K Srinivasa Rao, K N Jayaveera,
S Sailaja,  P Reddanna & D Bharat Reddy

 

 

 

 

 

 

 

2147

A novel approach to the synthesis of 4H-tetrazolo
[1,5-a][1,4]benzodiazepin-6-ones from 1,2,3-benzotri-azin-4-(3H)-ones

 

IPC: Int.Cl.8 C07D

Two  novel  routes have been developed for the synthesis of 4H-tetrazolo[1,5-a]1,4]benzodiazepin-6-ones 6a-b from
3-substituted1,2,3-benzotriazin-4-(3H)-ones 2a-b and 9.

 

 

 

Renu Gupta, Reenu Sirohi & D Kishore*

 

 

 

 

 

 

 

2151

Two new long chain compounds from Bauhinia variegata Linn

 

IPC: Int.Cl.8 A61K

Two new long chain compounds, heptatriacontan-12,13-diol 1 and dotetracont-15-en-9-ol 2 have been isolated from the leaves of Bauhinia variegata. Structures of these compounds have been elucidated by spectral data analyses and chemical studies.

 

 

 

 

R S Singh*, H S Pandey & Ghanshyam

 

 

 

 

 

 

 

2154

10-Methyl-n-heptacosane and diglucosyldirhamnoside from the stem bark of  Balanites aegyptiaca Delile

 

IPC: Int.Cl.8 A612K

A new long chain aliphatic compound, 10-methyl-n-heptacosane and a new sugar, diglucosyldirhamnoside have been isolated from the ethanolic extract of the stem bark of Balanites aegyptiaca. The structures of these compounds were elucidated by a combination of spectral methods (IR, MS, 1H and, l3C NMR).

 

 CH3

 

CH3 (CH2)8 CH (CH2)16 CH3

 

110-methyl-n-heptacosane

C24H42O19

2-Diglucosyldirhamnoside

 

 

M M Ansaria, J Ahmad, M Ali & S H Ansarib

 

 

 

 

 

 

 

2157

Regeneration of the carbonyl compounds from their semicarbazones using tetra-n-alkylammonium bromates

 

IPC: Int.Cl.8 C07C

Tetraalkylammonium bromates are prepared by a simple procedure and used for the oxidative regeneration of the parent carbonyl compound from their semicarbazones. Reaction conditions are simple and the deprotection gives satisfactory yield of the carbonyl compound.

 

 

 

 

Akashi Baruah, Utpal Nath, Satya Sandhya Das & Pranab Jyoti Das*

 

 

 

 

 

 

 

2161

Pentadecanoic acid β-D-glucoside from Clerodendrum inerme

 

IPC: Int.Cl.8 A61K

A new aliphatic glycoside, isolated from the hexane extract of aerial parts of Clerodendrum inerme, has been characterized as pentadecanoic acid-β-D-glucoside, on the basis of spectral data analyses and chemical studies. Stigmasterol glucoside was also isolated from the same extract for the first time from this plant species. The butanol extract afforded acacetin and apigenin.

 

 

 

 

R Pandey, R K Verma & M M Gupta*

 

 

 

 

Authors for correspondence are indicated by (*)

 

IPC: International Patent Classification

Int.Cl8.: International Classification, 8th Edition, 2006