Microbial cyclosophoraose as a catalyst for the synthesis of diversified indolyl 4H-chromenes via one-pot three component reactions in water

Green Chem., 2016, 18,3620-3627
DOI: 10.1039/C6GC00137H, Paper

Someshwar D. Dindulkar, Daham Jeong, Eunae Cho, Dongjin Kim, Seunho Jung
A novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic [small beta]-(1,2) glucan, was used for the synthesis of indolyl 4H-chromenes via a one pot three-component Knoevenagel-Michael addition-cyclization reaction in water under neutral conditions.

Someshwar D. Dindulkar,^a   Daham Jeong,^a   Eunae Cho,^a  Dongjin Kim^b and   Seunho Jung*^ac  

 *corresponding authors

^a

Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 143-701, South Korea
E-mail: shjung@konkuk.ac.kr

^b

Nelson Mandela African Institution of Science and Technology, PO box 447, Arusha, Tanzania

^c

Department of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, Seoul 143-701, South Korea

Green Chem., 2016,18, 3620-3627

DOI: 10.1039/C6GC00137H

As a novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic β-(1,2) glucan, was used for the synthesis of therapeutically important versatile indolyl 4H-chromenes via a one pot three-component Knoevenagel–Michael addition–cyclization reaction of salicylaldehyde, 1,3-cyclohexanedione/dimedone, and indoles in water under neutral conditions. A possible reaction mechanism through molecular complexation is suggested based on 2D ROESY NMR spectroscopic analysis. Moreover, green chemistry metric calculations were carried out for a model reaction, indicating the satisfactory greener approach of this method, with a low E-factor (0.18) and high atom economy (AE = 91.20%). The key features of this protocol are based on two critical factors where the first is to use a novel eco-friendly supramolecular carbohydrate catalyst and the second is its fine green properties such as compatibility with various substituted reactants, recyclability of the catalyst, chromatography-free purification, high product selectivity, and clean conversion with moderate to excellent yields in an aqueous medium.

 

 

//////Microbial cyclosophoraose, catalyst,  synthesis , diversified indolyl 4H-chromenes , one-pot three component reactions, water

Microbial cyclosophoraose as a catalyst for the synthesis of diversified indolyl 4H-chromenes via one-pot three component reactions in water

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Microbial cyclosophoraose as a catalyst for the synthesis of diversified indolyl 4H-chromenes via one-pot three component reactions in water

Green Chem., 2016, Advance Article DOI: 10.1039/C6GC00137H, Paper Someshwar D. Dindulkar, Daham Jeong, Eunae Cho, Dongjin Kim, Seunho Jung A novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic [small beta]-(1,2) glucan, was used for the synthesis of indolyl 4H-chromenes via a one pot three-component Knoevenagel-Michael addition-cyclization reaction in water under neutral conditions.

Someshwar D. Dindulkar,^a   Daham Jeong,^a   Eunae Cho,^a  Dongjin Kim^b and   Seunho Jung*^ac  

*Corresponding authors

^aInstitute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 143-701, South Korea
E-mail: shjung@konkuk.ac.kr

^bNelson Mandela African Institution of Science and Technology, PO box 447, Arusha, Tanzania

^cDepartment of Bioscience and Biotechnology, Microbial Carbohydrate Resource Bank (MCRB), Konkuk University, Seoul 143-701, South Korea

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC00137H

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00137H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

As a novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic β-(1,2) glucan, was used for the synthesis of therapeutically important versatile indolyl 4H-chromenes via a one pot three-component Knoevenagel–Michael addition–cyclization reaction of salicylaldehyde, 1,3-cyclohexanedione/dimedone, and indoles in water under neutral conditions. A possible reaction mechanism through molecular complexation is suggested based on 2D ROESY NMR spectroscopic analysis. Moreover, green chemistry metric calculations were carried out for a model reaction, indicating the satisfactory greener approach of this method, with a low E-factor (0.18) and high atom economy (AE = 91.20%). The key features of this protocol are based on two critical factors where the first is to use a novel eco-friendly supramolecular carbohydrate catalyst and the second is its fine green properties such as compatibility with various substituted reactants, recyclability of the catalyst, chromatography-free purification, high product selectivity, and clean conversion with moderate to excellent yields in an aqueous medium.

 

 

 

////////Microbial cyclosophoraose,  catalyst,  synthesis,  diversified indolyl 4H-chromenes, one-pot three component reactions, water

Solvent-free Mizoroki–Heck reactions and its application in the synthesis of Axitinib

A green method for the synthesis of a D-glucosamine-derived triazole@palladium catalyst is described. The synthesized catalyst containing a 2-pyridyl-1,2,3-triazole ligand was prepared via a click route in high yields and was explored in Heck cross-coupling reactions between different aryl halides and olefins under solvent-free conditions. The catalyst can be separated from the reaction mixture and reused at least six times with superior activity. In addition, using this protocol, the marketed drug Axitinib (antitumor) could be synthesized easily.

 

A novel D-glucosamine-derived pyridyl-triazole@palladium catalyst for solvent-free Mizoroki–Heck reactions and its application in the synthesis of Axitinib

Chao Shen,^ab   Hongyun Shen,^b   Ming Yang,^b   Chengcai Xia^b and   Pengfei Zhang*^b  

*Corresponding authors

^aCollege of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, China

^bCollege of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, China
E-mail: zpf100@163.com
Fax: +86-571-28862867
Tel: +86-571-28862867

Green Chem., 2015,17, 225-230

DOI: 10.1039/C4GC01606H

http://pubs.rsc.org/en/content/articlelanding/2015/gc/c4gc01606h/unauth#!divAbstract

Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyrans,

Scheme 1: Synthesis of 4H-benzo[b]pyran derivatives under MW irradiation.

 

Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyrans,

Organic Chemistry International
Volume 2014 (2014), Article ID 851924, 8 pages
http://dx.doi.org/10.1155/2014/851924

 

Sougata Santra, Matiur Rahman, Anupam Roy, Adinath Majee, and Alakananda Hajra
Volume 2014 (2014), Article ID 851924, 8 pages

http://www.hindawi.com/journals/oci/2014/851924/

A green and highly efficient method has been developed for the one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component condensation of aldehydes, 1,3-cyclic diketones, and malononitrile under MW irradiation without using any catalyst and solvent. This transformation presumably occurs by a sequential Knoevenagel condensation, Michael addition, and intramolecular cyclization. Operational simplicity, solvent and catalyst-free conditions, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure.

Scheme 2: Plausible reaction mechanism.

 

Novel Nickel-Based Catalyst Efficiently Splits Water

Researcher discovers inexpensive catalyst to produce oxygen and hydrogen gas.
(Credit: Kathy F. Atkinson / University of Delaware)

The University of Delaware’s Yushan Yan and his research group synthesized an inexpensive nickel-based catalyst that can split water into oxygen and hydrogen gas.

Nickel, which is cheap and abundant, is an attractive replacement for currently used precious metals.

SEE ALSO: EPFL Scientists Propose Cheaper Hydrogen Production Method

http://dailyfusion.net/2014/06/nickel-based-catalyst-29043/