Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

Meenakshi Singh; Abhijit Hazra; Yogesh P. Bharitkar; Ritu Kalia; Ashutosh Sahoo; Sneha Saha; V. Ravichandiran; Shekhar Ghosh; Nirup B. Mondal

doi:10.1039/C8RA02725K

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Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition†

Meenakshi Singh,^a Abhijit Hazra,

*^a Yogesh P. Bharitkar,

*^a Ritu Kalia,^a Ashutosh Sahoo,^b Sneha Saha,^a V. Ravichandiran,^a Shekhar Ghosh^b and Nirup B. Mondal^b

Author affiliations

* Corresponding authors

^a National Institute of Pharmaceutical Education and Research (NIPER), (IICB Campus), 4, Raja S. C. Mullick Road, Jadavpur, Kolkata – 700 032, India

^b Department of Organic and Medicinal Chemistry, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata – 700 032, India
E-mail: apuhazra@gmail.com, yogeshbharitkar@gmail.com

Abstract

Curcumin has been transformed to several diversely substituted bis-pyrrolizidino/thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via a sequential azomethine ylide cycloaddition reaction using isatins/acenaphthoquinone and proline/thioproline as the reagents. The products were separated via extensive chromatography and characterized by 1D/2D NMR and HRMS analysis.

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Article information

DOI: https://doi.org/10.1039/C8RA02725K
Article type: Paper
Submitted: 29 Mar 2018
Accepted: 16 May 2018
First published: 23 May 2018
This article is Open Access

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RSC Adv., 2018,8, 18938-18951

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Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

M. Singh, A. Hazra, Y. P. Bharitkar, R. Kalia, A. Sahoo, S. Saha, V. Ravichandiran, S. Ghosh and N. B. Mondal, RSC Adv., 2018, 8, 18938 DOI: 10.1039/C8RA02725K

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Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition†

Abstract

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Synthesis of diversely substituted bis-pyrrolizidino/ thiopyrrolizidino oxindolo/acenaphthyleno curcuminoids via sequential azomethine ylide cycloaddition

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