An efficient and more sustainable one-step continuous-flow multicomponent synthesis approach to chromene derivatives

Buchi Reddy Vaddula; Swathi Yalla; Michael A. Gonzalez

doi:10.1556/1846.2015.00015

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Journal of Flow Chemistry

Volume/Issue:: Volume 5: Issue 3

An efficient and more sustainable one-step continuous-flow multicomponent synthesis approach to chromene derivatives

Authors:

Buchi Reddy Vaddula

Buchi Reddy Vaddula Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN 37831, USA
U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 483, Cincinnati, OH 45268, USA

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Swathi Yalla

Swathi Yalla U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 483, Cincinnati, OH 45268, USA

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, and

Michael A. Gonzalez

Michael A. Gonzalez U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 483, Cincinnati, OH 45268, USA

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Pages:: 172–177

Online Publication Date:: Sep 2015

Publication Date:: 01 Sep 2015

Article Category:: Research Article

DOI:: https://doi.org/10.1556/1846.2015.00015

Keywords:: 2-aminochromenes; arylidenemalononitriles; flow reactor; 1,8-diazabicycloundec-7-ene (DBU); process intensification; Knoevenagel condensation

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A simple and rapid one-step continuous-flow synthesis route has been developed for the preparation of chromene derivatives from the reaction of aromatic aldehydes, α-cyanomethylene compounds, and naphthols. In this contribution, a one-step continuous-flow protocol in a ThalesNano H-Cube Pro™ has been developed for the preparation of these chromene derivatives. This arises from the multicomponent one-step reaction of aromatic aldehydes, α-cyanomethylene compounds, and naphthols. This flow protocol was optimized in 2-methyltetrahydrofuran, which is a more environmentfriendly solvent. The faster residence times (<2 min) coupled with elevated pressure (∼25 bar) results in an efficient, safer, faster, and modular reaction. Results obtained illustrate that this base-catalyzed reaction affords the respective chromene derivative products in very high yields. The products can then be easily purified by recrystallization, if desired.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)