4. Chemiluminescent organic compounds. Part I. Isomeric simple and complex hydrazides of phthalic acid and mode of formation of phthalazine and isoindole rings

Drew, H. D. K.; Hatt, H. H.

doi:10.1039/jr9370000016

Cited by 102 publications

(13 citation statements)

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“…The composition of the reaction mixtures and the purity of compounds obtained was checked by TLC on Alugram SIL G/UV 254 plates. N-Aminophthalimide was obtained by procedure [6].…”

Section: Methodsmentioning

confidence: 99%

Oxidative addition of N-aminophthalimide to styryl-1,2,4-oxadiazoles

et al. 2010

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The oxidation of N-aminophthalimide with lead tetraacetate in the presence of 5-[(Ε)-2-arylethenyl]-3-(4-methylphenyl)-1,2,4-oxadiazoles and 5-(4-methylphenyl)-3-[(Ε)-2-phenyl-ethenyl]-1,2,4-oxadiazole led to the formation of the corresponding (3-aryl-1-phthalimidoaziridin-2-yl)-(4-methylphenyl)-1,2,4-oxadiazoles. In the reaction with 3,5-distyryl-1,2,4-oxadiazole a mixture was obtained of two regioisomeric monoadducts and a diadduct in the ratio 80 : 15 : 5; at the use of 3 equiv of the aziridinating reagents only diadduct was isolated as a mixture of two diastereoisomers in the ~3 : 2 ratio that were separated by recrystallization.The oxidative phthalimido-aziridination of alkenylsubstituted pyrazoles and 1,3,4-oxadiazoles proceeds at the exocyclic C=C bond and affords cleanly the corresponding aziridinylazoles [1,2]. In this connection the evaluation of the applicability range and revealing the regular trends of this reaction as a general method for designing linearly connected polyheterocyclic systems containing aziridine fragment is an urgent task. To this end we selected styryl-substituted 1,2,4-oxadiazoles fairly different from its isomers, symmetric 1,3,4-oxadiazoles.Initial unsaturated 1,2,4-oxadiazoles IIa-IIe were obtained by procedure [3] through the thermal cyclization of acylation products of amidoximes Ia, Id prepared from p-tolunitrile or cinnamonitrile and hydroxylamine (Scheme 1) [3].The 1 H NMR spectra of styryl-1,2,4-oxadiazoles IIaIIe in the region δ 7.0-8.0 ppm contain doublets of the olefin protons with 3 J 15-17 Hz indicating the retention of the trans-location of these protons in the course of the cyclization. In their 13 C NMR spectra the carbon atoms of the heterocycle at δ 168-169 (C 3 ) and ~175 ppm (C 5 ) are characteristic; they are shifted downfield by 5-10 ppm compared with the carbon atoms of the isomeric 1,3,4-oxadiasoles (cf.[2]).The oxidative addition of the N-aminophthalimide to styryloxadiazoles IIa-IIe was carried out by the standard procedure adding in turns by small portions N-aminophthalimide and lead tetraacetate to the solution of the unsaturated compound in dichloromethane [2]. We established in the preliminary runs with IIa substrate (from the 1 H NMR spectra of the reaction mixtures) that at cooling the solution from the room temperature to -10°C the conversion of the initial compound considerably grew, but further cooling practically did not affect the rate of the process, therefore all subsequent reactions were performed at-10°C. The composition of separated R 1 = C 6 H 4 Me-p, R 2 = CH=CH-Ph (a), CH=CH-C 6 H 4 OMe-p (b), CH=CH-C 6 H 4 NO 2 -p (c); R 1 = CH=CH-Ph, R 2 = C 6 H 4 Me-p (d), CH=CH-Ph (e). Scheme 1.

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“…The composition of the reaction mixtures and the purity of compounds obtained was checked by TLC on Alugram SIL G/UV 254 plates. N-Aminophthalimide was obtained by procedure [6].…”

Section: Methodsmentioning

confidence: 99%

Oxidative addition of N-aminophthalimide to styryl-1,2,4-oxadiazoles

et al. 2010

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“…[11,12] N-Aminophthalimide (2) was obtained by the reaction of phthalimide and 96% hydrazine hydrate in ethyl alcohol. [13] Cyclohexene was prepared from cyclohexanone using an established method. [14] Reaction of Superoxide Ion Generated in situ with N-Amino…”

Section: S Singh and K N Singh 2598mentioning

confidence: 99%

Superoxide‐Mediated Synthesis ofN‐Aminoaziridines fromN‐Aminoheterocycles and Olefins

Singh

2005

Synthetic Communications

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“…Obviously, the formation of azines 8 and 9 is the result of decomposition of dihydrazides 6a and 6b with liberation of hydrazine (cf. [11][12][13][14]) which then reacts with diketone 2 or 3. Analogous transformation of dihydrazide 5 is responsible for the formation of linear products 11 and 12.…”

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confidence: 99%