Indoleninoxide, V. stabile 1-acyl-7,7a-dihydro-1h-azirino-[1, 2a] indole durch cycloaddition einiger alkine an 3h-indol-1-oxide

Synthesis and Reactivity of 2-(Carboxymethyl)aziridine Derivatives

“…Reaction of nitrones 50 with alkyl acetylenecarboxylates 51 via 1,3-dipolar cycloaddition resulted in selective and efficient synthesis of 4-isoxazoline-5-carboxylates 52 , which proved to be excellent precursors for synthesis of the corresponding N -alkyl- and N -aryl-2-oxalylaziridines 53 via a thermally induced 1,3-sigmatropic rearrangement (Scheme ). − …”

“…In accordance with the previous results, which led to isolation of aziridine 61, synthesis of tricyclic aziridine 66 starting from 3H-indole-N-oxide 63 has also been described. 57 Cycloaddition of 3H-indole-N-oxide 63 to ethyl phenylacetylenecarboxylate 64 afforded the tricyclic aziridine 66 in a highly regio-and stereoselective manner without isolation of the intermediate 4-isoxazoline-5-carboxylate 65 (Scheme 12). 57 The tricyclic aziridine 66 was obtained in high yield (88%).…”

“…57 Cycloaddition of 3H-indole-N-oxide 63 to ethyl phenylacetylenecarboxylate 64 afforded the tricyclic aziridine 66 in a highly regio-and stereoselective manner without isolation of the intermediate 4-isoxazoline-5-carboxylate 65 (Scheme 12). 57 The tricyclic aziridine 66 was obtained in high yield (88%).…”

One‐Pot Stereoselective Synthesis of 2‐Acylaziridines and 2‐Acylpyrrolidines from N‐(Propargylic)hydroxylamines

“…These results suggest that a radical pathway should be ruled out. Although the precise reaction mechanism of this rearrangement is not yet clear, the [1,3]‐sigmatropic rearrangement proposed for the original Baldwin rearrangement without metal salts is the probable pathway for affording the cis ‐2‐acylaziridines 8c,d,f. The reaction might be activated by the coordination of nitrogen to the copper center, thereby leading to a weakening of the NO bond (Figure 1).…”

Reactions of dibenzoylacetylene with N-alkylnitrones, heteroaromatic N-oxides, and diazo and azoxy compounds

“…The latter peak is assigned to the corresponding nitrile oxide ions, produced from "Elemental analyses (C, , N) were submitted for review and agree well with the theoretical values. 6 Yields belong to method b in the Experimental Section. 'Lit.…”