Metal-Free Regioselective Oxa-Michael Approach to Access Spirooxindole-Fused Tetrahydrofuran/Tetrahydropyran through [3+2]/ [4+2] Spirocyclization of Methyleneindolinones with Haloalcohols

被引：1

作者：

Savekar, Amol T. ^{[1
]}

Gaikwad, Ramesh A. ^{[1
]}

Waghmode, Suresh B. ^{[1
]}

机构：

[1] Savitribai Phule Pune Univ, Dept Chem, Pune 411007, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 13期

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITIONS; DIELS-ALDER REACTION; PHOSPHINES SYNTHESIS; CASCADE REACTION; 3+2 ANNULATION; CONSTRUCTION; OXINDOLES; ISATINS; 3-VINYLINDOLES; SCAFFOLDS;

D O I：

10.1021/acs.joc.4c00659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient one-pot metal-free, base-catalyzed method has been developed for the regioselective [3 + 2]/[4 + 2] annulation reactions of electrophilic methyleneindolinones with haloalcohols to furnish spirooxindole derivatives under mild reaction conditions. This reaction afforded the corresponding products with two contiguous stereocenters including a quaternary center in good to excellent yield (up to 95%) with moderate to good diastereoselectivities (up to 12.5:1 dr) with complete regioselectivity.

引用

页码：9389 / 9404

页数：16

共 12 条

[1] Metal-Free Approach for Oxa-spirocyclohexadienones through [3+2]/[4+2] ipso-Cyclization of para-Quinone Methides with Halo Alcohols
Gaikwad, Ramesh A.
Savekar, Amol T.
Waghmode, Suresh B.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (14): : 9987 - 10001
[2] Transition Metal-Free Synthesis of 3-Acylquinolines through Formal [4+2] Annulation of Anthranils and Enaminones
Zhang, Kai-Ling
Yang, Jia-Cheng
Guo, Qin
Zou, Liang-Hua
CATALYSTS, 2023, 13 (04)
[3] Metal-Free Tandem Approach for Triazole-Fused Diazepinone Scaffolds via [3+2]Cycloaddition/C-N Coupling Reaction
Majeed, Kashif
Wang, Lingna
Liu, Bangjie
Guo, Zijian
Zhou, Fengtao
Zhang, Qiuyu
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 207 - 222
[4] Tf2NH-Catalyzed Formal [3+2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
Zhao, Yingying
Hu, Yancheng
Wang, Chunxiang
Li, Xincheng
Wan, Boshun
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3935 - 3942
[5] A Green Approach for 1,2,3-Triazole-Fused Quinolinones via Metal-Free Cascade [3+2] Cycloaddition/C-N Coupling Reaction
Majeed, Kashif
Zhou, Fengtao
Liu, Chaoyi
Guo, Zijian
Dong, Penghui
Zhang, Qiuyu
CHEMISTRYSELECT, 2022, 7 (31):
[6] Metal-free [3+2] cycloaddition of azides with Tf2C=CH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles
Alcaide, Benito
Almendros, Pedro
Lazaro-Milla, Carlos
CHEMICAL COMMUNICATIONS, 2015, 51 (32) : 6992 - 6995
[7] PIDA-promoted metal-free [3+2] heteroannulation of β-ketothioamides with 4-hydroxy coumarins: chemo-/regioselective access to furo[3,2-c]chromen-4-ones at room temperature
Yadav, Anup Kumar
Yadav, Dhananjay
Kumar, Vipin
Ray, Subhasish
Singh, Maya Shankar
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (21) : 4326 - 4331
[8] Metal-Free Air Oxidation in a Convenient Cascade Approach for the Access to Isoquinoline-1,3,4(2H)-triones
Di Mola, Antonia
Tedesco, Consiglia
Massa, Antonio
MOLECULES, 2019, 24 (11):
[9] Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution
Fu, Zhicheng
Sun, Simin
Yang, Anjian
Sun, Fang
Xu, Jiaxi
CHEMICAL COMMUNICATIONS, 2019, 55 (87) : 13124 - 13127
[10] A simple route to tetracyclic oxazepine-fused pyrroles via metal-free [3+2] annulation between dibenzo[b,f][1,4]oxazepines and aqueous succinaldehyde
Choudhary, Sachin
Singh, Anoop
Yadav, Jyothi
Mir, Nisar A.
Anthal, Sumati
Kant, Rajni
Kumar, Indresh
NEW JOURNAL OF CHEMISTRY, 2019, 43 (02) : 953 - 962

← 1 2 →