29745-97-9Relevant articles and documents
Enantioselective synthesis of cyclic and linear diamines by imine cycloadditions
Chang, Tsung-Che,Pradipta, Ambara R.,Tanaka, Katsunori
, p. 1160 - 1168 (2020)
Imine is one of the most versatile functional groups in chemistry and biochemistry fields. Although many biochemical reactions involve imine formation, the inherently unstable property of N-alkyl-α,β-unsaturated imines still hindered their utilization in organic synthesis. In this article, we described that the N-alkyl-α,β-unsaturated imines, which prepared from alkylamines and acrolein, could smoothly react through [4 + 4] cycloaddition to give eight-membered diazacyclooctane derivatives in excellent yields. Under a similar condition, in the presence of formaldehyde, the [4 + 2] and [4 + 2 + 2] cycloadditions could lead to the formation of six-membered hexahydropyrimidine or eight-membered triazacyclooctanes, depending on the substituent of aldehydes. Moreover, an easy functional group manipulation of the cyclic products obtained from these cycloadditions can provide variously substituted chiral linear diamines. We can utilize these novel reactivities to reveal the unknown and essential properties of many biological processes that involve N-alkyl-unsaturated imines.
ASYMMETRIC NITROGEN-41 STEREOCHEMISTRY OF BICYCLIC 1,2-CIS-DIAZIRIDINES
Shustov, G.V.,Denisenko, S.N.,Chervin, I.I.,Asfandiarov, N.L.,Kostyanovsky, R.G.
, p. 5719 - 5732 (2007/10/02)
The twisting of 5- and 6-membered rings in bicyclic cis-diaziridines-1,5-diazabicyclo(3.1.0)hexanes 12-17 and 1,6-diazabicyclo(4.1.0)heptane 18-is a rapid process in the time scale of 1H- and 13C-NMR even at -80 deg C.According to the 1H- and 13C-NMR spectra, 1,5-diazabicyclo(3.1.0)hexanes 12, 13, 15a,b and 16a, b do, exist mostly in the boat form; only the introduction of endo substituents into position 3 or 6 leads to the population of the chair, as is the case with 14 and 17. 2,4-Dialkyl substituted 1,5-diaza- and 1,3,5-triazabicyclo(3.1.0)hexanes are formed via a transition cyclization state similar in its geometry to the initial chair-shaped N-chlorodi(tri)azanes.
