Efficient and environmentally sustainable domino protocol for the synthesis of diversified spiroheterocycles with privil
- PDF / 1,564,399 Bytes
- 11 Pages / 595.276 x 790.866 pts Page_size
- 68 Downloads / 156 Views
ORIGINAL ARTICLE
Efficient and environmentally sustainable domino protocol for the synthesis of diversified spiroheterocycles with privileged heterocyclic substructures using bio‑organic catalyst in aqueous medium Kanchan Verma1 · Yogesh Kumar Tailor1 · Sarita Khandelwal1 · Esha Rushell1 · Monu Agarwal1 · Mahendra Kumar1 Received: 16 August 2019 / Accepted: 30 September 2019 © Springer Nature Switzerland AG 2019
Abstract An efficient and environmentally sustainable synthetic protocol has been presented to synthesize structurally diverse spiroxindoles spiroannulated with indenopyrroloimidazoles, pyranopyrroloimidazoles, chromenopyrroloimidazoles, and imidazopyrrolopyrimidines involving three-component reaction of isatins, hydantoin, and β-diketones in the presence of green and sustainable bio-organic catalyst, β-amino acid, 2-aminoethanesulfonic acid (taurine), in aqueous media. The synthetic efficiency, operational simplicity, and reusability of catalyst make the present synthetic protocol cost effective, time efficient, and eco-friendly to synthesize molecules with structural diversity and molecular complexity and expected to contribute significantly not only to drug discovery research but also to pharmaceutical and medicinal chemistry. Keywords Bio-organic catalyst · Environmentally sustainable · Multicomponent reactions · Pyrroloimidazoles · Spiroheterocycles
Introduction Multicomponent reactions (MCRs) have attracted considerable interest in modern organic synthesis in view of their exceptional synthetic efficiency and high atom economy to construct bioactive molecules with structural diversity and drug-like complexity. The synthetic efficiency and operational simplicity of MCRs make them cost effective, time efficient, and eco-friendly in comparison with conventional multistep synthesis [1]. Thus, MCRs have acquired unique place in diversity-oriented synthesis (DOS) and biology-oriented synthesis (BOS) with their applications not only in medicinal chemistry but also especially in drug discovery research, combinational chemistry, and natural
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-09999-4) contains supplementary material, which is available to authorized users. * Mahendra Kumar [email protected] 1
Department of Chemistry, University of Rajasthan, Jaipur, India
product synthesis [2–5]. The synthesis of structurally diverse complex molecules in one-pot and single operation avoiding the use of hazardous conventional organic solvents as reaction medium has become very attractive in organic synthesis in view of their concerns with the environmental sustainability and use of the newly synthesized structurally diverse drug-like complex molecules in drug discovery research. In addition to environmental concern, it is probably better to perform the reactions under solventfree conditions, but when solvent is essentially required, water is considered the best choice as a solvent [2, 6–9] since it is an inexpensive, nontoxic, and nonfla
Data Loading...
