Lipase‐Initiated Tandem Biginelli Reactions via in situ‐Formed Acetaldehydes in One Pot: Discovery of Single‐Ring Deep Blue Luminogens

A facile approach for the synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones was developed by a tandem multi‐component reaction (MCR) in one pot. This approach involves two steps, lipase‐catalyzed in situ generation of acetaldehyde and the Biginelli reaction in turn. Several control experiments were perfo...

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Veröffentlicht in:	Advanced synthesis & catalysis 2017-10, Vol.359 (19), p.3397-3406
Hauptverfasser:	Zhang, Wei, Wang, Na, Yang, Zeng‐Jie, Li, Yan‐Rong, Yu, Yuan, Pu, Xue‐Mei, Yu, Xiao‐Qi
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetaldehyde Candida antarctica lipase B Cascade chemical reactions enzyme catalysis fluorescence Libraries Lipase Modularity one-pot synthesis Solid state Synthesis tandem reaction
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container_issue	19
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container_title	Advanced synthesis & catalysis
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creator	Zhang, Wei Wang, Na Yang, Zeng‐Jie Li, Yan‐Rong Yu, Yuan Pu, Xue‐Mei Yu, Xiao‐Qi
description	A facile approach for the synthesis of 3,4‐dihydropyrimidin‐2(1H)‐ones was developed by a tandem multi‐component reaction (MCR) in one pot. This approach involves two steps, lipase‐catalyzed in situ generation of acetaldehyde and the Biginelli reaction in turn. Several control experiments were performed using acetaldehydes directly to explore the possible mechanism of this procedure. Moreover, owing to the distinct modularity and highly efficient features of the MCR, it can assemble libraries of structurally diverse products (yields up to 98% under the optimized conditions in this paper) and provides an exceptional synthesis tool for the discovery of the minimal deep‐blue luminogen in the solid state, namely, a single ring.
doi_str_mv	10.1002/adsc.201700599
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This approach involves two steps, lipase‐catalyzed in situ generation of acetaldehyde and the Biginelli reaction in turn. Several control experiments were performed using acetaldehydes directly to explore the possible mechanism of this procedure. Moreover, owing to the distinct modularity and highly efficient features of the MCR, it can assemble libraries of structurally diverse products (yields up to 98% under the optimized conditions in this paper) and provides an exceptional synthesis tool for the discovery of the minimal deep‐blue luminogen in the solid state, namely, a single ring.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201700599</doi><tpages>10</tpages></addata></record>
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subjects	Acetaldehyde Candida antarctica lipase B Cascade chemical reactions enzyme catalysis fluorescence Libraries Lipase Modularity one-pot synthesis Solid state Synthesis tandem reaction
title	Lipase‐Initiated Tandem Biginelli Reactions via in situ‐Formed Acetaldehydes in One Pot: Discovery of Single‐Ring Deep Blue Luminogens
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