Beckmann Fragmentation of Diphenylcarbamoylated N-Aryldiphenacylamine Dioximes. New Method for the Synthesis of Imidazooxadiazolones

Coşkun, Necdet; Tat, Fatma; Güven, Özden Özel

doi:10.1080/00397919908085909

Cited by 10 publications

(6 citation statements)

References 12 publications

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“…26a The scope of the above reaction was also investigated with a tetraoxime of the type 4 (Scheme 3), which was obtained as a single isomer by a reported procedure. 31 The reaction of 4 with cyanoborohydride affords an interesting molecule with two piperazyl units linked by a phenyl ring, 5. The 1 H and 13 C NMR spectra of 5 confirm that the molecule is symmetrical (Scheme 3, Table 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN

et al. 2011

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Section: Resultsmentioning

confidence: 99%

Synthesis of novel N-hydroxy heterocycles via intramolecular reductive cyclization of diketoximes by NaBH3CN

et al. 2011

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“…For general background, see: Sevagapandian et al (2000); Marsman et al (1999); Coşkun et al (1999); Karle et al (1996); Etter et al (1990); Chertanova et al (1994); Balsamo et al (1990); Lipshutz (1986); Holan et al (1984); Forman (1964). For related literature, see: Sarıkavaklı et al (2007); Ö zel Gü ven et al (2004a,b).…”

Section: Related Literaturementioning

confidence: 99%

“…Furan is a relatively highly reactive heteroaromatic compound and is frequently used as an intermediate in organic synthesis (Lipshutz, 1986). In literature, Beckmann fragmentation reaction of N-aryl-N,N-diphenacylamine dioximes has been reported as a new method for the synthesis of imidazooxadiazolones which are imidazole derivatives (Coşkun et al, 1999).…”

Section: Tablementioning

confidence: 99%

N,N-Bis[2-(2-furyl)-2-(hydroxyimino)ethyl]aniline

2007

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Key indicators: single-crystal X-ray study; T = 298 K; mean (C-C) = 0.004 Å; R factor = 0.042; wR factor = 0.110; data-to-parameter ratio = 9.5.In the crystal structure of the title compound, C 18 H 17 N 3 O 4 , intramolecular C-HÁ Á ÁO hydrogen bonds cause the formation of two planar five-membered rings, which are also coplanar with the adjacent rings. The oxime units have E configurations and their bond lengths and angles compare well with those in related compounds. In this configuration, the oxime groups are involved as donors in O-HÁ Á ÁN hydrogen bonds, linking the molecules into chains extending approximately parallel to the c axis and stacked along the b axis. Related literatureFor general background, see: Sevagapandian et al.

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“…For general background, see: Mann et al (2001); Roth et al (1997); Evans et al (1996); Chen et al (1993); Saito et al (1993); Awouters et al (1983); Brandstrom et al (1985); Preston (1974); Lipshutz (1986); Coşkun et al (1999); Sevagapandian et al (2000); Forman (1964); Holan et al (1984); Balsamo et al (1990); Chertanova et al (1994) ; Sarıkavaklı et al (2007). For bond length data, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…Beckmann fragmentation reaction of N-aryl-N,N-diphenacylamine dioximes has been reported as a new method for the synthesis of imidazooxadiazolones which are imidazole derivatives (Coşkun et al, 1999).…”

Section: Data Collectionmentioning

confidence: 99%