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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA16-06446S" target="_blank" >GA16-06446S: Od aminokyselin k molekulárním skafoldům inspirovaných přírodou</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

—

Svazek periodika

21

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

5

Strana od-do

1-5

Kód UT WoS článku

000456349200001

EID výsledku v databázi Scopus

2-s2.0-85059878909