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Review | Special issue | Vol 97, No. 2, 2018, pp.668-685
Published online, 1st June, 2018
DOI: 10.3987/REV-18-SR(T)4
Cycloaddition Reactions of N-Alkyl-α,β-unsaturated Imines: Facile Preparation of Azaheterocycles for Synthesis and Biological Applications

Ambara R. Pradipta, Liliya Latypova, Dilyara Chulakova, Ivan Smirnov, Almira Kurbangalieva, and Katsunori Tanaka*

*Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan


In this review, we will describe the utilization of formal [4 + 4] cycloaddition reaction of N-alkyl-,-unsaturated imines derived from acrolein and biogenic alkylamines to synthesize 2,6,9-triazabicyclo[3.3.1]nonanes and 1,5-diazacyclooctanes. We also include here a new structural data of 1,5-diazacyclooctane determined by X-ray crystallography. Biological examination of 1,5-diazacyclooctanes revealed for the first-time its role in inhibition of amyloid- (A) 1-40 fibrillization. Eventually, we also found that when substituted or unsubstituted acrolein is reacted with chiral ethanolamine in the presence of formaldehyde, then hexahydropyrimidines or 1,3,5-triazacyclooctanes were produced in high yield and stereoselectivity through formal [4 + 2] or [4 + 2 + 2] cycloaddition reactions. Lastly, simple functional group manipulations of the cycloaddition products can be used to synthesize chiral 1,3-diamines, which could not be simply accessed by other methods.