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Citation: WANG Yu, LU Ming. Modified Synthesis of Four Kinds of Azabicyclo Compounds[J]. Chinese Journal of Applied Chemistry, ;2012, 29(4): 397-401. doi: 10.3724/SP.J.1095.2012.00244 shu

Modified Synthesis of Four Kinds of Azabicyclo Compounds

WANG Yu ,
LU Ming ^,

1.
Department of Chemistry, Nanjing University of Science and Technology, Nanjing 210094, China

Corresponding author: LU Ming,
Received Date: 9 June 2011
Available Online: 11 October 2011
Fund Project: 国家自然科学基金委员会和中国工程物理研究院联合基金资助项目(11076017) (11076017)

Azabicyclo compounds of 1,4-benxodiazine,pyridopyrazine,1H-benzimidazole,3H-imidazopyridine were prepared from o-phenylenediamine or 2,3-diaminopyridine reacted with carbonyl compounds.The effects of reaction medium,pH,time and other factors on the reactions were invesitigated.The results showed that the yield of pyridopyrazine could reach 89.4% when refluxed in propanol for 1 h at pH=9 adjusted by methanol sodium.The yields for 1,4-benxodiazine could be increased to 98.3% in aqueous medium with pH=9 adjusted by sodium sulfite at 60℃ after 40 min reaction.Here,the purification of target product could be achieved via a low temperature standing process instead of the vacuum distillation method.The optimized conditions for the other two compounds are:refluxing o-phenylenediamine for 2 h in 88% formic acid solution yielding 1H-benzimidazole with 92% yield;refluxing 2,3-diaminopyridine with triethoxy methane for 3 h followed by adding concentrated hydrochloric acid for another 1 h giving 3H-imidazopyridine with 84.2% yield.
- azabicyclo compounds,
- synthesis,
- condensation
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