2001
DOI: 10.1016/s0040-4039(01)01406-x
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A convenient synthesis of 1H-2,3-benzoxazines by an acid-catalyzed intramolecular Mitsunobu reaction

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Cited by 8 publications
(6 citation statements)
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“…Oximes contain the NOH group that can act as the nucleophile in the Mitsunobu reaction. Thus, an intramolecular Mitsunobu procedure was utilized for the synthesis of herbicidal benzoxazines 493 from 2(hydroxyiminomethyl)benzyl alcohols 492 (Scheme a) . It was surmised that the Z -isomer was the one that reacted.…”
Section: Miscellaneous Reactionsmentioning
confidence: 99%
“…Oximes contain the NOH group that can act as the nucleophile in the Mitsunobu reaction. Thus, an intramolecular Mitsunobu procedure was utilized for the synthesis of herbicidal benzoxazines 493 from 2(hydroxyiminomethyl)benzyl alcohols 492 (Scheme a) . It was surmised that the Z -isomer was the one that reacted.…”
Section: Miscellaneous Reactionsmentioning
confidence: 99%
“…The use of a weak acid catalyst has recently been advocated to improve the yield of the Mitsunobu reaction. [31] When the procedure was repeated with the addition of 0.2 equiv. of 4-nitrophenol the naphthopyran 14b was obtained in an improved yield (27%).…”
mentioning
confidence: 99%
“…Fortunately, the synthesis of the desired amines ( 9 ) was successfully accomplished via oximes (Table ). Thus, the treatment of the selected triarylethanones ( 3j − m ) with hydroxylamine hydrochloride afforded the intermediate oximes ( 8 ) as a mixture of anti and syn isomers, which were, without further purification, submitted to the Zn/HCOOH (aq) reductive conditions, leading to the corresponding amines ( 9 ) with moderate to high overall yields.
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Section: Resultsmentioning
confidence: 99%