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Synthesis and bioactivity of 6‐bromo‐2‐(substituted)‐3‐(1‐phenyl‐ethyl)‐ 3,4‐dihydro‐1 H ‐ isophosphinoline 2‐chalcogenides
Author(s) -
Srinivasulu K.,
Babu B. Hari,
Kumar K. Suresh,
Reddy C. Bhupendra,
Raju C. Naga,
Rooba D.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450319
Subject(s) - chemistry , triethylamine , phosphine , toluene , hydrogen peroxide , aryl , medicinal chemistry , sulfur , alkyl , organic chemistry , catalysis
ynthesis of 6‐bromo‐2‐(substituted)‐3‐(1‐phenyl‐ethyl)‐3,4‐dihydro‐1 H ‐isophosphinoline 2‐chalco‐genides derivatives (6) were synthesized from 2‐[(1‐phenylethylamino)methyl]‐4‐bromophenol ( 1 ) by reaction with aryl/alkyl phosphoro dichloridates ( 2 ) in the presence of triethylamine at 55°C to 60°C to obtained the title compounds ( 6a‐g ). The title compounds ( 6h‐j ), were prepared via intermediate route. Few other title compounds ( 8a‐c ) were accomplished through a two step synthetic route involving 1 with dichlorophenyl phosphine ( 2a ) and dichloroethyl phosphine ( 2a,b ) in the presence of triethylamine in dry toluene under N 2 atmosphere to form the corresponding trivalent phosphorus intermediate (7) . In the second step they were further converted to the corresponding chalcogenides 8a‐c by reaction with hydrogen peroxide, sulfur and selenium respectively. They exhibited significant antibacterial, fungal and insecticidal activity.