Convenient Construction of Spiro[pyrazole‐4,1′‐pyrido[2,1‐a]isoquinoline] and Spiro[pyrazole‐4,4′‐pyrido[1,2‐a]quinoline] via Three‐Component Reaction

The three‐component reaction of isoquinoline, dialkyl but‐2‐ynedioate and 4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐ones in acetonitrile at room temperature gave functionalized spiro[pyrazole‐4,1′‐pyrido[2,1‐a]isoquinolines] in satisfactory yields with cis/cis‐diastereoisomer as major product. On the o...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2021-10, Vol.6 (39), p.10537-10541
Main Authors: Fang, Hui‐Ling, Sun, Jing, Yan, Chao‐Guo
Format: Article
Language:English
Subjects:
electron-deficient alkyne
Huisgen's 1,4-dipole
multicomponent reaction
pyrazolone
spiro compounds
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Summary:The three‐component reaction of isoquinoline, dialkyl but‐2‐ynedioate and 4‐arylidene‐5‐methyl‐2‐phenylpyrazol‐3‐ones in acetonitrile at room temperature gave functionalized spiro[pyrazole‐4,1′‐pyrido[2,1‐a]isoquinolines] in satisfactory yields with cis/cis‐diastereoisomer as major product. On the other hand, the similar three‐component reaction with quinoline afforded both cis/cis‐ and cis/trans‐isomeric spiro[pyrazole‐4,4′‐pyrido[1,2‐a]quinolines] in nearly comparable yields. The reaction was finished with in situ generation of Huisgen’ 1,4‐dipole, sequential Michael addition and annulation reaction process. The three‐component reaction of quinoline (isoquinoline), dialkyl but‐2‐ynedioate and unsaturated pyraozol‐3‐ones provided a convenient synthetic protocol for functionalized spiro compounds in good yields.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202102255