US EPA

6360312 

Journal Article 

Synthesis, NMR analysis and X-ray crystal structure of novel 1,5-dibenzyl-1,2,5,6-tetrahydro-1,5-diazocines 

Tan, Hb; Li, H; Xu, J; Song, Gt; Meng, Jp 

2019 

Yes 

Journal of Molecular Structure
ISSN: 0022-2860
EISSN: 1872-8014 

1188 

7-13 

10.1016/j.molstruc.2019.03.079 

WOS:000464988000002 

http://www.sciencedirect.com/science/article/pii/S002228601930359X
Exit
 

Novel eight-membered 1,5-dibenzyl-1,2,5,6-tetrahydro-1,5-diazocines (4a-4f) were prepared by a new three-component aza-annulation as one-pot method from paraformaldehyde, ethyl propiolate, and benzylamine. Unique structure of products, an easy experimental workup, the use of simple and available starting materials, and the high atom economy are the main advantages of this method. The target compound was isolated and unambiguously confirmed by NMR spectra (1D-NMR and 2D-NMR), high-resolution mass spectrometry, and single-crystal X-ray diffraction analysis. Furthermore, the products possess N-benzyl-protected secondary amines and ß-enamine esters, which can serve in further functionalizations to produce molecular diversity for use in medicinal and synthetic chemistry. 

1,5-Diazocines; One-pot synthesis; Eight-membered ring; NMR analysis; X-ray crystal structure