66447-83-4Relevant academic research and scientific papers
Phosphine-Catalyzed Interrupted Morita–Baylis–Hillman Reaction and Switchable Domino Reactions of α-Substituted Activated Olefins with Formaldehyde and Mechanism Elucidation
Gu, Jing,Xiao, Ben-Xian,Ouyang, Qin,Du, Wei,Chen, Ying-Chun
, p. 155 - 160 (2019/01/21)
3-Olefinic oxindoles can undergo interrupted Morita-Baylis-Hillman reaction with formaldehyde. Apart from the previous reported dephosphoration to access reductive aldol-type products, here we uncovered that completely different pathways were followed by tuning the substitutions of 3-olefinic oxindoles. In combination with formalin, an unexpected domino phosphorus-ylide formation, aldol-type addition, hemeacetal formation and O-substitution process was observed to produce 1,3-dioxolane derivatives. Moreover, a switchable sequence to produce formate derivatives via a key hydride transfer process was furnished by simply replacing formalin with paraformaldehyde. Density functional theory calculations were conducted to well elucidate the catalytic reaction mechanism.
Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine e
Li, De-Feng,Liu, Kun,Jiang, Yi-Xuan,Gu, Yan,Zhang, Jing-Ru,Zhao, Li-Ming
supporting information, p. 1122 - 1125 (2018/02/23)
The development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available pren
Squaramide-Catalyzed Enantioselective Cascade Approach to Bispirooxindoles with Multiple Stereocenters
Zhao, Bo-Liang,Du, Da-Ming
supporting information, p. 3992 - 3998 (2016/12/30)
A bifunctional squaramide-catalyzed Michael/Michael cascade reaction for the construction of spirotetrahydrofuran bispirooxindoles was developed. The products were obtained in moderate to excellent yields with excellent diastereo- and enantioselectivities
One-pot synthesis of new spiro[cyclopropane-1,3′-[3H]indol]- 2′(1′H)-ones from 3-phenacylideneoxindoles
Shaabanzadeh, Masoud,Khabari, Faranak
scheme or table, p. 949 - 953 (2010/09/03)
(Chemical Equation Presented) In a one-pot procedure, the 3-phenacylideneoxindoles 1a-d were reacted with hydrazine and then in situ with lead(IV) acetate and new diastereoisomers of spiro[cyclopropane-1,3′-[3H] indol]-2′(1′H)-ones were prepared. Compounds 1a-d underwent a highly diastereoselective cyclopropanation leading to diastereoisomers 2a-d. These new compounds containing both 2-oxindole and cyclopropane moieties may be valuable in medicinal chemistry.
