ChemInform Abstract: Facile Diastereoselective Synthesis of Phosphonate Esters Bearing Cyclic or Acyclic Amides.

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

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Diastereoselective Synthesis of Novel Optically Active Five Membered O- and N-heterocyclic Compounds

Letters in Organic Chemistry ◽

10.2174/157017812800221744 ◽

2012 ◽

Vol 9 (2) ◽

pp. 81-88 ◽

Cited By ~ 1

Author(s):

Ervin Kovacs ◽

Ferenc Farkas ◽

Angelika Thurner ◽

Aron Szollosy ◽

Ferenc Faigl

Keyword(s):

Heterocyclic Compounds ◽

Optically Active ◽

Diastereoselective Synthesis

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An Efficient One-Pot Enantio- and Diastereoselective Synthesis of Heterocycles

Angewandte Chemie International Edition ◽

10.1002/anie.200290019 ◽

2002 ◽

Vol 41 (24) ◽

pp. 4693-4697 ◽

Cited By ~ 41

Author(s):

Barry M. Trost ◽

Michelle R. Machacek

Keyword(s):

Diastereoselective Synthesis ◽

One Pot

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A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones

Organics ◽

10.3390/org2020010 ◽

2021 ◽

Vol 2 (2) ◽

pp. 107-117

Author(s):

Mattia Forchetta ◽

Valeria Conte ◽

Giulia Fiorani ◽

Pierluca Galloni ◽

Federica Sabuzi

Keyword(s):

Metal Oxides ◽

Phosphonic Acid ◽

Organic Molecules ◽

Building Blocks ◽

Reaction Conditions ◽

Phosphonic Acids ◽

Sustainable Improvement ◽

Phosphonate Esters ◽

First Time ◽

Complex Organic

Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications.

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