2007
DOI: 10.3184/030823407x198401
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Reaction between 5-Benzylidene-2,2-Dimethyl-1,3-Dioxane-4,6-Dione and Tert-butyl Isocyanide in the Presence of Ethane-1,2-diol or Catechol

Abstract: tert-Butyl isocyanide undergoes a smooth reaction with 5-benzylidene-2,2-dimethyl-1,3-dioxane-4,6-diones (benzylidene Meldrum's acids) in the presence of ethane-1,2-diol or catechol to produce functionalised N-tertbutyl-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-aryl-ethanamides or bis-(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1-aryl-2oxoethyl]-malonates in good yields.

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Cited by 7 publications
(14 citation statements)
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“…The 1 H-decoupled 13 C NMR spectrum of 4a showed 10 distinct resonances in agreement with the proposed structure. The 1 H-decoupled 31 P NMR spectrum of 4a * Correspondent.…”
supporting
confidence: 81%
See 1 more Smart Citation
“…The 1 H-decoupled 13 C NMR spectrum of 4a showed 10 distinct resonances in agreement with the proposed structure. The 1 H-decoupled 31 P NMR spectrum of 4a * Correspondent.…”
supporting
confidence: 81%
“…IR spectra were measured on a Shimadzu IR-460 spectrometer. 1 H, 13 C, and 31 P NMR spectra were measured with a Bruker DRX-300 Avance spectrometer at 300.1, 75.5, and 121.5 MHz. Compounds 1-3 were obtained From Fluka and were used without further purification.…”
Section: Methodsmentioning
confidence: 99%
“…Diethyl 2-[(cyclohexylimino) (3-methyl-4-oxo-5,5-diphenyl-2-thioxoimidazolidin-1-yl) Dimethyl 2-[(cyclohexylimino) (3-methyl-4-oxo-5,5-di-p-tolyl-2thioxoimidazolidin-1-yl) 6.28;N,7.48;S,5.71. Found: C,66.15;H,6.35;N,7. …”
Section: Scheme 2 Experimentalmentioning
confidence: 99%
“…IR: 1625, 1520, 1446 cm −1 . 1 H NMR (300 MHz, CDCl 3 ): 0.97 (3 H, t, 3 J = 6.1, Me), 1.36 (2 H, m, CH 2 ), 1.73 (2 H, m, CH 2 ), 2.02 (3 H, s, Me), 2.50 (3 H, s, Me), 3.84 (2 H, t, 3 J = 7.3, CH 2 N), 6.50 (1 H, s, CH), 7.30-7.37 (5 H, m, 5 CH) 13. C NMR (75 MHz, CDCl 3 ): 11.9 (Me), 14.9 (Me), 20.3 (CH 2 ), 31.4 (Me), 33.2 (CH 2 ), 46.7 (CH 2 N), 119.8 (CH), 21.9 (C), 125.9 (C), 126.9 (CH), 128.5 (2 CH), 129.7 (2 CH), 135.1 (C), 136.9 (C), 197.9 (C=O).…”
mentioning
confidence: 98%