Traceless solid-phase synthesis of 1’H-spiro[pyrrolidine-3,2′-quinazolin]-2-ones and 1’H-spiro[piperidine-3,2′-quinazolin]-2-ones via lactamization of 1,2-dihydroquinazoline-2-carboxylates

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F19%3A73596972" target="_blank" >RIV/61989592:15310/19:73596972 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00145" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00145</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acscombsci.8b00145" target="_blank" >10.1021/acscombsci.8b00145</a>

Result language
angličtina
Original language name
Traceless solid-phase synthesis of 1’H-spiro[pyrrolidine-3,2′-quinazolin]-2-ones and 1’H-spiro[piperidine-3,2′-quinazolin]-2-ones via lactamization of 1,2-dihydroquinazoline-2-carboxylates
Original language description
We present the solid-phase synthesis of 1,2-dihydroquinazoline-2-carboxylate derivatives with a quaternary carbon in position 2 and their subsequent cyclization in solution into compounds with unique 3D architectures and pharmacological relevance – spiroquinazolines, namely, 1’H-spiro[pyrrolidine-3,2′-quinazolin]-2-ones and 1’H-spiro[piperidine-3,2′-quinazolin]-2-ones. Acyclic precursors were prepared from commercially available building blocks: protected amino acids (2,4-diaminobutyric acid and ornithine), 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The crucial step of the synthesis was a base-mediated tandem reaction including C-arylation followed by cyclization into indazole oxides, and the formation of a 5-membered heterocycle was accomplished by ring expansion into quinazolines. These derivatives were cyclized into spiro compounds in solution after cleavage from the resin.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA16-06446S" target="_blank" >GA16-06446S: From Amino Acids to Nature-Inspired Molecular Scaffolds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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