Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 6797-13-3, is researched, SMILESS is CCC1=NC2=CC=CC=C2O1, Molecular C9H9NOJournal, Article, Journal of the American Chemical Society called Carbon-Carbon Bond Cleavage of Diynes through the Hydroamination with Transition Metal Catalysts, Author is Shimada, Tomohiro; Yamamoto, Yoshinori, the main research direction is benzoxazole preparation; aminophenyl cyclocondensation diyne; ruthenium carbonyl hydroamination catalyst; hydroamination catalyst transition metal catalyst; carbon carbon bond cleavage diyne.Reference of 2-Ethylbenzo[d]oxazole.
The C-C bond cleavage of terminal and internal diynes takes place readily in the presence of catalytic amounts of Ru3(CO)12 or Pd(NO3)2 and of 2-aminophenol, giving the corresponding benzoxazoles and ketones in good to high yields. Thus, reaction of 2-H2NC6H4OH with RCCCCH [R = hexyl, decyl, cyclohexyl, Me3C, PhCH2CH2, (Me2CH)3SiO(CH2)4, Cl(CH2)3] in MeOH containing Ru3(CO)12 and NH4PF6 gave mixtures of 2-methylbenzoxazole and the C-2 substituted benzoxazoles I in 58-98% yields in addition to acetone and RCOMe. The substituted aminophenols II (R1 = 4-NO2, 4-Cl, 4-Me, 4-MeO, 5-NO2, 5-Me, 3-Me) reacted similarly with 1,3-decadiyne to give methylbenzoxazoles III and hexylbenzoxazoles IV. The two different modes of bond cleavage in these reactions are cleavage of an alkyne C-C triple bond and cleavage of the C-C single bond between the two alkyne groups.
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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem