Synthesis of 7′-Arylidenespiro[indoline-3,1′-pyrrolizines]
and 7′-Arylidenespiro[indene-2,1′-pyrrolizines] via
[3 + 2] Cycloaddition and β‑C–H Functionalized
Pyrrolidine
Ying Huang
Hui-Lin Fang
Yi-Xin Huang
Jing Sun
Chao-Guo Yan
10.1021/acs.joc.9b01920.s002
https://acs.figshare.com/articles/dataset/Synthesis_of_7_-Arylidenespiro_indoline-3_1_-pyrrolizines_and_7_-Arylidenespiro_indene-2_1_-pyrrolizines_via_3_2_Cycloaddition_and_C_H_Functionalized_Pyrrolidine/9879539
The
acetic acid catalyzed three-component reaction of pyrrolidine,
aromatic aldehydes, and 3-arylideneoxindolin-2-ones in refluxing toluene
afforded functionalized 7′-arylidenespiro[indoline-3,1′-pyrrolizines]
in good yields and with high diastereoselectivity. The similar three-component
reaction with 2-arylidene-1,3-indanediones also gave 7′-arylidenespiro[indene-2,1′-pyrrolizines]
in good yields. However, the reaction with 3-phenacylideneoxindoles
resulted in a mixture of spiro[indoline-3,1′-pyrrolizines]
and 7′-arylidene-substituted spirooxindoles in moderate yields.
The reaction mechanism included generation of azomethine ylides, β-C–H
functionalization of pyrrolidine, and sequential [3 + 2] cycloaddition.
The obtained spirooxindole derivatives were investigated by in vitro
evaluation against mouse colon cancer cells CT26 and human liver cancer
cells HepG2 by MTT assay.
2019-09-19 13:36:43
arylidenespiro
MTT
pyrrolidine
spirooxindole
liver cancer cells HepG 2
three-component reaction
mouse colon cancer cells CT 26
Arylidenespiro
yield
3- arylideneoxindolin -2-ones