1966
DOI: 10.1002/jhet.5570030429
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Synthesis and rearrangement of dibenz[b,e][1,4]oxazepin‐6(11H)‐one, depsazidone

Abstract: A large number of naturally occurring compounds of the polysubstituted 2-hydroxyphenoxybenzoic acid lactone (depsidone) type were isolated by Asahina ( 2 ) from lichens. Noyce and Weldon and others ( 3 ) succeeded in the synthesis of the parent lactone, depsidone (Ia) and several simple homologs. Accordingly we became interested in the possibility of synthesizing a nitrogen analog, which we have termed depsazidonc (Ib), and which does not occur naturally either as the parent o r a s derivatives. 0 U R l a . x … Show more

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Cited by 8 publications
(2 citation statements)
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“…Tomioka et al studied the photolysis of the azide of 9 in cyclohexane that afforded 2-phenyl-1H-indoline exclusively in low yield 24 . The decomposition of phenyl 2-azidobenzoate 15 (obtained from phenyl 2-aminobenzoate 25 ) with triflic acid was slow when compared with the above examples and the only isolable compound was phenyl 2-amino-5-trifluoromethanesulfonylbenzoate 16 in 25% yield. With TFA under the same conditions most of the starting azide was recovered.…”
Section: Resultsmentioning
confidence: 99%
“…Tomioka et al studied the photolysis of the azide of 9 in cyclohexane that afforded 2-phenyl-1H-indoline exclusively in low yield 24 . The decomposition of phenyl 2-azidobenzoate 15 (obtained from phenyl 2-aminobenzoate 25 ) with triflic acid was slow when compared with the above examples and the only isolable compound was phenyl 2-amino-5-trifluoromethanesulfonylbenzoate 16 in 25% yield. With TFA under the same conditions most of the starting azide was recovered.…”
Section: Resultsmentioning
confidence: 99%
“…64 The crucial cyclization step has been affected using various strategies e.g. aza-Wittig cyclization, 65 intramolecular dehydration, 66 and ring expansion reactions, 67 however special conformational restrictions are usually required in order to obtain reasonable yields from direct cyclization of acyclic precursors. 63,68 For example, Banfi Tröger's base (75), a bridged variant of a dibenzo [b,f] [1,5]diazocine, has a chiral aromatic cleft structure with a unique ability to host guests and as a result act as a supramolecular receptor (Figure 1.11).…”
Section: 5-benzodiazocinesmentioning
confidence: 99%