A Formal Condensation and [4+1] Annulation Reaction of 3-Isothiocyanato Oxindoles with Aza-o-Quinone Methides

Gui, Hou-Ze1,2; Wu, Xiao-Yun1,2; Wei, Yin3; Shi, Min1,2,3,4

2019-11-07

10.1002/adsc.201901124

ADVANCED SYNTHESIS & CATALYSIS   影响因子和分区

1615-4150

1615-4169

A formal condensation and [4+1] annulation reactions of 3-isothiocyanato oxindoles with aza-o-quinone methides have been reported in this paper for the first time. The use of Na2CO3 as a base exclusively gave the corresponding condensed products in good yields, which can be smoothly transformed into the formal [4+1] annulation products if using DBU as a base. In addition, isothiocyanate could serve as a leaving group during the nucleophilic addition reaction has been disclosed. The two bases play different roles in the reaction and the desired cyclized products can be also obtained in good to high yields in a one-pot manner under mild conditions.

condensation [4+1] annulation reaction aza-o-quinone methide 3-isothiocyanato oxindole spirooxindole

SCI ; IC ; CCR

英语

通讯

Fundamental Research Funds for the Central Universities[222201717003]

Chemistry

Chemistry, Applied ; Chemistry, Organic

WOS:000494876600001

WILEY-V C H VERLAG GMBH

Web of Science

1.East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
2.East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
3.Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Lu, Shanghai 200032, Peoples R China
4.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Gui, Hou-Ze,Wu, Xiao-Yun,Wei, Yin,et al. A Formal Condensation and [4+1] Annulation Reaction of 3-Isothiocyanato Oxindoles with Aza-o-Quinone Methides[J]. ADVANCED SYNTHESIS & CATALYSIS,2019,361(23):5466-5471.

Gui, Hou-Ze,Wu, Xiao-Yun,Wei, Yin,&Shi, Min.(2019).A Formal Condensation and [4+1] Annulation Reaction of 3-Isothiocyanato Oxindoles with Aza-o-Quinone Methides.ADVANCED SYNTHESIS & CATALYSIS,361(23),5466-5471.

Gui, Hou-Ze,et al."A Formal Condensation and [4+1] Annulation Reaction of 3-Isothiocyanato Oxindoles with Aza-o-Quinone Methides".ADVANCED SYNTHESIS & CATALYSIS 361.23(2019):5466-5471.