109925-95-3Relevant academic research and scientific papers
Synthesis of Pyrrole Derivatives from 5,6-Dihydro-4H-1,2-oxazines via Reductive Deoxygenation by Use of Fe3(CO)12
Nakanishi, Saburo,Otsuji, Yoshio,Itoh, Keiji,Hayashi, Nobuaki
, p. 3595 - 3600 (2007/10/02)
α-Bromooximes such as α-bromoacetophenone oxime and ethyl 3-bromo-2-(hydroxyimino)propanoate react with enamines to give 5,6-dihydro-4H-1,2-oxazines in good yields.Dihydro-1,2-oxazine derivatives are also obtained by the reaction of α-bromooximes with vinyl ethers and silyl enol ethers in the presence of Na2CO3.Dihydro-1,2-oxazines can be converted into pyrrole derivatives via reductive deoxygenation by treating with Fe3(CO)12 in moderate to excellent yields.Iron carbonyl complexes other than Fe3(CO)12 are also effective for the pyrrole-forming reaction.The efficiency of the complexes for this reaction decreases in the or der: Fe3(CO)12 >> Et3NH > Fe2(CO)9 >> Fe(CO)5.Both of the dihydro-1,2-oxazine- and pyrrole-forming reactions can be carried out in a single flask, giving pyrrole derivatives in good yields.
Efficient Synthesis of 6-Trimethylsiloxy- and 6-(Trimethylsilyl)methyl-3-phenyl-5,6-dihydroxy-4H-1,2-oxazines by Cycloaddition of α-Nitrosostyrene to Silyl Enol Ethers and Allyltrimethylsilane
Hippeli, Claudia,Reissig, Hans-Ulrich
, p. 77 - 79 (2007/10/02)
The title compounds 3 are prepared in good yield from silyl enol ether 1 and α-nitrosostyrene 2, generated in situ from α-chloroacetophenone oxime 4.Allyltrimethylsilane smoothly affords cycloadduct 5 which could be opened to the unsturated ketone 6 or am
