Intermolecular double Michael reaction to construct 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.0^2,7]dodec-2(7)-ene-4-carbonitrile

Abstract

1-azabicyclo[2.2.2]octan-3-one. HCl (1) reacts with ylidene nitrile through photo- thermal reaction conditions to give 4-benzyl-5-imino-3-phenyl-6-oxa-1-aza-tricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile. (3) via intermolecular double Micheal reaction, whereas, 5-imino-3-phenyl-6-oxa-1-azatricyclo[6.2.2.02,7]dodec-2(7)-ene-4-carbonitrile (4) was achieved via thermal conditions only.

Behavior of 2‐iminothiazolidin‐4‐one with different reagents

“…In light of the pharmaceutical importance of several fused bicyclic ring systems, the most important are those containing a nitrogen ringjunction, where a nitrogen is common to two rings [11,12], such as levamisole (imidazo [2,1-b]thiazole) (4) [12]. So, the objective of this work was directed to annulate 2-imino-4-thiazolidinone (5) via cycloaddition followed by cyclo-condensation reaction, as a part of our continuing interest in the synthesis of biologically active molecules [13][14][15][16][17].…”