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Haloacetylated enol ethers: 3 . Synthesis of 3,3a,4,5,6,7‐hexahydro‐3‐halomethyl benzoisoxazoles
Author(s) -
Martins Marcos A. P.,
Flores Alex F. C.,
Freitag RogŔRio,
Zanatta Nilo
Publication year - 1995
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.5570320305
Subject(s) - chemistry , isoxazole , regioselectivity , substituent , enol , hydroxylamine , ketone , enol ether , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , financial economics , economics
The investigation of the halomethyl group effect on the regiochemistry of the reaction of 2‐acetylcyclo‐hexanones 1a‐d and β‐methoxyvinyl trifluoro methyl ketone derivative 2a with hydroxylamine to afford 3,3a,4,5,6,7‐hexahydro‐3‐halomethyl‐3‐hydroxy[2,1]benzoisoxazoles 3a‐c , and the respective dehydrated compounds 4a‐c , is reported. Compounds 1a‐c, 2a proved to be versatile building blocks for the regiospecific synthesis of isoxazole derivatives having a 3‐halomethyl substituent, in good yields.