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Synthesis and Antifungal Activity of Some New Quinazoline and Benzoxazinone Derivatives
Author(s) -
Shalaby Alyaa A.,
ElKhamry Abdel Momen A.,
Shiba S.A.,
Ahmed Abdel Aal Alm Eldeen Abdalah,
Hanafi Awaref A.
Publication year - 2000
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/1521-4184(200011)333:11<365::aid-ardp365>3.0.co;2-2
Subject(s) - chemistry , quinazolinone , benzamide , acylation , organic chemistry , alkylation , hydrazide , isoxazole , reagent , carbamate , quinazoline , catalysis
The hitherto unknown 2‐isopropyl‐6,8‐dibromo‐4 H ‐3,1‐benzoxazin‐4‐one ( 2 ) was subjected to condensation with either primary or secondary amines affording the benzamide derivatives ( 3 — 7 ), while with alcohols in presence of the base, corresponding esters were obtained ( 8 and 9 ). Acylation of the hydrazide ( 12 ) or its cyclized form ( 13 ) gave ( 14 — 17 ). The quinazolinone derivative ( 18 ) was obtained either when ( 12 ) was reacted with nitrous acid or via fusion of ( 2 ) with ammonium acetate. The thione ( 20 ) which was obtained via reaction of ( 18 ) with Lawesson's reagent, was subjected to either alkylation yielding ( 21 — 25 ) or desulphurization with primary amines affording ( 26 and 27 ). Treatment of ( 18 ) as well as ( 20 ) with a chlorinating agent provided ( 29 , 30 ) and ( 28 , 29 ) mixtures, respectively. Ten of our compounds were examined against Sclerotium cepivorum as well as Botrytis allii on PDA media. These compounds showed a significant reduction of mycelial growth and scleratia number of these fungi which cause the white rot and neck rot diseases of onion.