Synthesis and antimicrobial activity of some oxazaphosphinine oxides

B Siva Kumar,C Devendranath Reddy,M V Narayan Reddy,A U Ravi Sankar,G Chandra Sekhar Reddy,C Suresh Reddy

doi:10.3998/ark.5550190.0009.c13

B Siva Kumar, C Devendranath Reddy + Show 4 more

Open Access

https://doi.org/10.3998/ark.5550190.0009.c13

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Abstract

A new family of phosphorus heterocycle, namely 2-substituted 3-[4-(2-oxo-3,4-dihydro-2λ 5 benzo[e][1,3,2]oxazaphosphinin-3-yl)phenyl]-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinin-2oxides (5a–j) has been synthesized by the condensation of 2-[[4-(2-hydroxy-benzylamino)phenylamino]methyl]phenol (1) with phosphorus oxychloride in presence of triethylamine in dry tetrahydrofuran, followed by the reaction with various phenols 3a–j. Alternatively, some of these compounds 5a-e were prepared by the cyclocondensation of 1 with aryl phosphorodichloridates 4a–e. All title compounds were characterized by elemental and spectral analyses. Their antimicrobial activity was also evaluated.

Highlights

Organophosphorus heterocycles containing O and N in a six-membered ring have gained much attention ever since cyclophosphamide was discovered as anti-cancer drug.1 Compounds of this class have high anti-tumor activity,2–5 significant bioactivity,6 and outstanding medicinal properties.7 The significant activity of all these compounds was accredited to the presence of sixmembered heterocyclic rings
All compounds were characterized by elemental, IR, H, 13C and 31P NMR and mass spectral analysis
Some products 5 were prepared by condensation of 1 with aryl phosphorodichloridates8 4a–e in the presence of triethylamine in dry THF

Summary

Introduction

Organophosphorus heterocycles containing O and N in a six-membered ring have gained much attention ever since cyclophosphamide was discovered as anti-cancer drug.1 Compounds of this class have high anti-tumor activity,2–5 significant bioactivity,6 and outstanding medicinal properties.7 The significant activity of all these compounds was accredited to the presence of sixmembered heterocyclic rings. NMR spectra of compounds 5a–j exhibit multiplets in the range δ 6.19–8.17 for aromatic protons.

Results

Conclusion