NDLI: Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindoles] by use of the Huisgen reaction

Content Provider	Springer Nature Link
Author	Chen, Gang Miao, Yan qing Zhou, Rui Zhang, Li Zhang, Jie Hao, Xiao jiang
Copyright Year	2012
Abstract	The Huisgen reaction has been used to synthesize five-membered heterocyclic compounds in high yield and with high regio and stereoselectivity. In the synthesis of spiro [pyrrolidine-2,3′-oxindole] derivatives from isatin, α-amino acids, and (E)-β-phenyl nitroolefins, two regioisomers were obtained in each reaction. The regioselectivity of the major product was found to be different from that in reported work, and was investigated at the B3LYP/6-311G* level of theory. On the basis of this new finding, several conditions, for example molar ratio, solvent, and temperature, which affect the regioselectivity of this reaction were investigated; the results obtained are discussed. It was found that the regioselectivity of this reaction was affected by solvent and temperature, irrespective of the ratio of the reactants. Low temperature and high solvent polarity leads to high regioselectivity, and protic solvents result in higher yield and regioselectivity. These results are of benefit for regioselective synthesis of some compounds.
Starting Page	2445
Ending Page	2450
Page Count	6
File Format	PDF
ISSN	09226168
Journal	Research on Chemical Intermediates
Volume Number	39
Issue Number	6
e-ISSN	15685675
Language	English
Publisher	Springer Netherlands
Publisher Date	2012-08-30
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Huisgen reaction Regioselectivity Regioisomer Spiro [pyrrolidine-2,3′-oxindole] Catalysis Physical Chemistry Inorganic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindole] compounds by [3+2] cycloaddition

Theoretical study of the regioselectivity of the Huisgen reaction

Spiro[pyrrolidine-2,3′-oxindole] derivatives synthesized by novel regionselective 1,3-dipolar cycloadditions

A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3′-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides

A tandem Aldol-Diels-Alder reaction accelerated in water: An approach to the Catalyst-Free One-Pot synthesis of spiro Thio-Oxindoles

Synthesis and regiochemistry of spiro indane-1,3-dione compounds

The Huisgen Reaction of Azomethine Ylide to Isatins: A Facile Synthesis of Spiro-oxindoles

An efficient synthesis of 1′,4′-dihydro-2′H-spiro[azetidin-2,3′-quinolin]-2′-one

Spiro[pyrrolidine-2,3'-oxindole] derivatives synthesized by novel regionselective 1,3-dipolar cycloadditions.

Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindoles] by use of the Huisgen reaction

Similar Documents

Theoretical study of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindole] compounds by [3+2] cycloaddition

Theoretical study of the regioselectivity of the Huisgen reaction

Spiro[pyrrolidine-2,3′-oxindole] derivatives synthesized by novel regionselective 1,3-dipolar cycloadditions

A Facile One-Pot Construction of Succinimide-Fused Spiro[Pyrrolidine-2,3′-Oxindoles] via 1,3-Dipolar Cycloaddition Involving 3-Amino Oxindoles and Maleimides

A tandem Aldol-Diels-Alder reaction accelerated in water: An approach to the Catalyst-Free One-Pot synthesis of spiro Thio-Oxindoles

Synthesis and regiochemistry of spiro indane-1,3-dione compounds

The Huisgen Reaction of Azomethine Ylide to Isatins: A Facile Synthesis of Spiro-oxindoles

An efficient synthesis of 1′,4′-dihydro-2′H-spiro[azetidin-2,3′-quinolin]-2′-one

Spiro[pyrrolidine-2,3'-oxindole] derivatives synthesized by novel regionselective 1,3-dipolar cycloadditions.

Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindoles] by use of the Huisgen reaction