An efficient Passerini tetrazole reaction (PT-3CR)

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC00910G, Communication

Ajay L. Chandgude, Alexander Domling
A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three-component reaction (PT-3CR) has been developed.

An efficient Passerini tetrazole reaction (PT-3CR)

see
http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00910G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

An efficient Passerini tetrazole reaction (PT-3CR)

Ajay L. Chandgude^a and   Alexander Dömling*^a  

*

Corresponding authors

^a

Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen, The Netherlands 
E-mail: a.s.s.domling@rug.nl
Web: http://www.drugdesign.nl/

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC00910G

 A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three-component reaction (PT-3CR) has been developed. It comprises the reaction of an aldehyde/ketone, an isocyanide and a TMS-azide in methanol:water (1:1) as the solvent system. The use of sonication not only accelerated the rate of the reaction but also provided good to excellent quantitative yields. This reaction is applicable to a broad scope of aldehydes/ketones and isocyanides.

  
Ajay L. Chandgude

• 
  University of Groningen

  Groningen Research Institute of Pharmacy (GRIP)

  Groningen, Netherlands

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Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

React. Chem. Eng., 2016, Advance Article
DOI: 10.1039/C6RE00059B, Paper

Open Access

  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Nicholas Holmes, Geoffrey R. Akien, A. John Blacker, Robert L. Woodward, Rebecca E. Meadows, Richard A. Bourne
Self-optimising flow reactors combine online analysis with evolutionary feedback algorithms to rapidly achieve optimum conditions.

Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

Self-optimising flow reactors combine online analysis with evolutionary feedback algorithms to rapidly achieve optimum conditions. This technique has been applied to the final bond-forming step in the synthesis of AZD9291, an irreversible epidermal growth factor receptor kinase inhibitor developed by AstraZeneca. A four parameter optimisation of a telescoped amide coupling followed by an elimination reaction was achieved using at-line high performance liquid chromatography. Optimisations were initially carried out on a model compound (2,4-dimethoxyaniline) and the data used to track the formation of various impurities and ultimately propose a mechanism for their formation. Our protocol could then be applied to the optimisation of the 2-step telescoped reaction to synthesise AZD9291 in 89% yield.

Paper

Self-optimisation of the final stage in the synthesis of EGFR kinase inhibitor AZD9291 using an automated flow reactor

Nicholas Holmes,^a   Geoffrey R. Akien,^ab   A. John Blacker,^ac  Robert L. Woodward,^d   Rebecca E. Meadows^d and  Richard A. Bourne*^acd  

*Corresponding authors

^aInstitute of Process Research and Development, School of Chemistry, University of Leeds, Leeds, UK
E-mail: r.a.bourne@leeds.ac.uk

^bDepartment of Chemistry, Faraday Building, Lancaster University, Lancaster, UK

^cSchool of Chemical and Process Engineering, University of Leeds, Leeds, UK

^dAstraZeneca Pharmaceutical Development, Silk Road Business Park, Macclesfield, UK

React. Chem. Eng., 2016, Advance Article

DOI: 10.1039/C6RE00059B

http://pubs.rsc.org/en/Content/ArticleLanding/2016/RE/C6RE00059B#!divAbstract

Scheme 1 Synthesis of the model acrylamide 6 via the β-chloroamide 5 intermediate.

Scheme 2 Proposed mechanisms to dimers 8a and 8b. The observation of a peak corresponding to 7suggested a Rauhut–Currier mechanism to 8b but subsequent LC-MS-MS analysis showed the major dimer to most likely be 8a. All observed peaks from offline LC-MS are displayed.

///////Self-optimisation, synthesis, EGFR kinase inhibitor, AZD9291,  automated flow reactor

Small but Mighty: Boron Nanoparticles

Small but Mighty: Boron Nanoparticles

Nanoparticles for hydrogen generation from water at room temperature

Read more


http://www.chemistryviews.org/details/news/9273321/Small_but_Mighty_Boron_Nanoparticles.html

• Boron Nanoparticles for Room-Temperature Hydrogen Generation from Water,
  Parham Rohani, Seongbeom Kim, Mark T. Swihart,
  Adv. Energy Mater. 2016.
  DOI: 10.1002/aenm.201502550

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Catalytic Nanotube Reactors

Catalytic Nanotube Reactors

Iron-noble metal nanoparticles in silica nanotubes catalyze styrene hydrogenation

Read more


http://www.chemistryviews.org/details/ezine/9297261/Catalytic_Nanotube_Reactors.html

• Preparation of Magnetic Tubular Shape Nanoreactors for Highly Efficient Catalysis,
  Wei-Guo Song, Shuliang Yang, Li Peng, Changyan Cao, Fang Wei, Jian Liu, Ya-Nan Zhu, Chang Liu, Xiaoshi Wang,
  Chem. Asian J. 2016.
  DOI: 10.1002/asia.201600454

//

Alkenylation of Pyridylmethylesters

Alkenylation of Pyridylmethylesters

Palladium-catalyzed vinylation under mild conditions

Read more

http://www.chemistryviews.org/details/news/9301151/Alkenylation_of_Pyridylmethylesters.html

• Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides,
  Xiaodong Yang, Byeong-Seon Kim, Minyan Li, Patrick J. Walsh,
  Org. Lett. 2016.
  DOI: 10.1021/acs.orglett.6b00815

A pot-economical and diastereoselective synthesis involving catalyst-free click reaction for fused-triazolobenzodiazepines

Green Chem., 2016, 18,2642-2646
DOI: 10.1039/C6GC00497K, Communication

Xiaofeng Zhang, Sanjun Zhi, Wei Wang, Shuai Liu, Jerry P. Jasinski, Wei Zhang
A pot-economical synthesis involving two [3 + 2] cycloadditions for diastereoselective synthesis of novel triazolobenzodiazepine-containing polycyclic compounds.
The content of this RSS Feed (c) The Royal Society of Ch

A pot-economical and diastereoselective synthesis involving catalyst-free click reaction for fused-triazolobenzodiazepines

A pot-economical and diastereoselective synthesis involving catalyst-free click reaction for fused-triazolobenzodiazepines

Xiaofeng Zhang,^a   Sanjun Zhi,^b   Wei Wang,^c   Shuai Liu,^a  Jerry P. Jasinski^d and   Wei Zhang*^a  

*

Corresponding authors

^a

Centre for Green Chemistry and Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, USA 
E-mail: wei2.zhang@umb.edu

^b

Jiangsu Key Laboratory for the Chemistry of Low-Dimensional Materials, Huaiyin Normal University, Huaian, PR China

^c

School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, PR China

^d

Department of Chemistry, Keene State College, Keene, USA

Green Chem., 2016,18, 2642-2646

DOI: 10.1039/C6GC00497K

A pot-economical synthesis involving sequential [3 + 2] cycloadditions of an azomethine ylide and an azide–alkyne (click reaction) has been developed for diastereoselective synthesis of novel triazolobenzodiazepine-containing polycyclic compounds. A new example of catalyst-free click chemistry of non-strained alkynes is also disclosed.

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9-(1H-indol-3-yl)-5-methoxy-3,3- dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one

• 

  
  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.

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

 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

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

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, Advance Article

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.

 9-(1H-indol-3-yl)-5-methoxy-3,3- dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one (4a):

 (2-hydroxy-3-methoxybenzaldehyde 1, Dimedone 2

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