AbstractTwo‐dimensional nmr techniques were used for the complete assignment of 13C nmr spectra of pyrrolo‐[1,2‐f]‐, pyrazolo[1,5‐f]‐, and 1,2,4‐triazolo[1,5‐f]phenanthridines.

AbstractTreatment of the phenylhydrazones (I) with acid yields the pyrazoloquinolinones (II) or pyrazolo‐quinolines (III).

AbstractThe 1,2,4‐thiadiazoles (III), (VI), and (IX) are prepared from ethoxycarbonyl isothiocyanate (II) and the amino heterocycles (I), (IV), and (VII) either directly or via the addition products (V) and (VIII).

AbstractThe β‐aminoketones (Ia) and (Ib) rearrange in the presence of Na‐ethoxide to give pyrimidine N‐oxides (II), which are reduced to give the pyrimidines (III).

The behaviour of N-(5-R-1,2,4-oxadiazol-3-yl)-β-enamino ketones towards rearrangement has been investigated. In the presence of anionic reagents in ethanol solution, they rearrange to pyrimidine N-oxides. The synthesis and hydrolytic ring opening of a [1,2,4]oxadiazolo[2,3-a]pyrimidinium system is also reported.

AbstractDas Benzoyl‐oxadiazol (I) kondensiert mit 1,1‐Diphenylhydrazin (II) zu den stereoisomeren Hydrazonen (III) und (IV).

AbstractThe behaviour of (E)‐ and (Z)‐N,N‐diphenylhydrazones and O‐Methyloximes of 3‐benzoyl‐5‐phenyl‐1,2,4‐oxadiazole has been studied. When refluxed in benzene, or in dioxane‐water (1:1), the (Z)‐N,N‐diphenylhydrazone 8Z gave the indazole 11 or the substituted semicarbazide 12, respectively. The O‐methyloxime 14Z did not give any rearrangement. A criticism of the oximation reaction of 3‐benzoyl‐5‐phenyl‐1,2,4‐oxadiazole is also reported.

Aus den Isoxazolyl‐ketonen (I) erhält man mit Phenylhydrazin (II) über die isomeren Hydrazone (III) und (IV) beim Erhitzen die Triazole (V) in guten Ausbeuten.

AbstractThe reaction of 3‐benzoyl‐5‐phenylisoxazole (4) and 3‐acetyl‐5‐methylisoxazole (5) with phenylhydrazine and N‐methyl‐N‐phenylhydrazine has been investigated and the reactivity of (E)‐ and (Z)‐phenylhydrazones and N‐methyl‐N‐phenylhydrazones has been studied.

Chemischer InformationsdienstVolume 13, Issue 15 Reviews ChemInform Abstract: MONONUCLEAR HETEROCYCLIC REARRANGEMENTS M. RUCCIA, M. RUCCIASearch for more papers by this authorN. VIVONA, N. VIVONASearch for more papers by this authorD. SPINELLI, D. SPINELLISearch for more papers by this author M. RUCCIA, M. RUCCIASearch for more papers by this authorN. VIVONA, N. VIVONASearch for more papers by this authorD. SPINELLI, D. SPINELLISearch for more papers by this author First published: April 13, 1982 https://doi.org/10.1002/chin.198215358AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume13, Issue15April 13, 1982 RelatedInformation

Abstract3‐Benzoyl‐5‐phenyl‐1,2,4‐oxadiazole (I) with phenylhydrazine in acetic acid gives the two geometrical isomers, phenylhydrazones II‐Z and II‐E, which have been characterized by uv‐visible, ir, and nmr spectra. The possible II‐E ⇌ II‐Z isomerization as well as the rearrangement of II‐Z and of II‐E into 2,5‐diphenyl‐4‐benzoylamino‐1,2,3‐triazole (III) has been pointed out.

AbstractAus den Oxadiazolen (I) entstehen thermisch die Umlagerungsprodukte (II), die zu den Aminen (III) verseift werden können.

Chemischer InformationsdienstVolume 10, Issue 31 Heterocyclic Compounds ChemInform Abstract: MONONUCLEAR HETEROCYCLIC REARRANGEMENTS. PART III. REARRANGEMENT OF THE P-METHOXYPHENYLHYDRAZONE AND THE M-NITROPHENYLHYDRAZONE OF 3-BENZOYL-5-PHENYL-1,2,4-OXADIAZOLE IN DIOXANE/WATER IN THE PS+ RANGE 3.8-11.5 D. SPINELLI, D. SPINELLISearch for more papers by this authorV. FRENNA, V. FRENNASearch for more papers by this authorA. CORRAO, A. CORRAOSearch for more papers by this authorN. VIVONA, N. VIVONASearch for more papers by this authorM. RUCCIA, M. RUCCIASearch for more papers by this author D. SPINELLI, D. SPINELLISearch for more papers by this authorV. FRENNA, V. FRENNASearch for more papers by this authorA. CORRAO, A. CORRAOSearch for more papers by this authorN. VIVONA, N. VIVONASearch for more papers by this authorM. RUCCIA, M. RUCCIASearch for more papers by this author First published: July 31, 1979 https://doi.org/10.1002/chin.197931239Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References D. SPINELLI, V. FRENNA, A. CORRAO, N. VIVONA, M. RUCCIA, MONONUCLEAR HETEROCYCLIC REARRANGEMENTS. PART III. REARRANGEMENT OF THE P-METHOXYPHENYLHYDRAZONE AND THE M-NITROPHENYLHYDRAZONE OF 3-BENZOYL-5-PHENYL-1,2,4-OXADIAZOLE IN DIOXANE/WATER IN THE PS+ RANGE 3.8-11.5, J. Heterocycl. Chem., 1979, 16, 359. DOI: 10.1002/jhet.5570160231; 10.1002/jhet.5570160231 CASWeb of Science®Google Scholar Volume10, Issue31July 31, 1979 ReferencesRelatedInformation

AbstractThe first example of a mononuclear heterocyclic rearrangement involving an XYZ = CCN side‐chain sequence is reported. The 3‐(o‐aminophenyl)‐, and 3‐(o‐methylaminophenyl)‐5‐methyl‐1,2,4‐oxadiazoles (3a,b) gave a thermally induced rearrangement into 3‐acylaminoindazoles (4a,b). On the other hand, the 3‐(o‐acetylaminophenyl)‐5‐methyl‐1,2,4‐oxadiazole (3c) produced a base induced rearrangement into 3‐acetylaminoindazole (4a).