Synthesis and spectroscopic and structural characterization of spiro[indoline-3,3′-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkene
| Autor: | Jairo Quiroga, Pablo E. Romo, Justo Cobo, Christopher Glidewell |
|---|---|
| Přispěvatelé: | University of St Andrews. School of Chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
crystal structure
synthesis Crystal structure Ring (chemistry) Supramolecular assembly Inorganic Chemistry chemistry.chemical_compound Synthesis NMR spectroscopy Stereochemistry spiro[- indoline-3 30-indolizine] Materials Chemistry QD Physical and Theoretical Chemistry molecular conformation Reaction mechanism chemistry.chemical_classification Alkene Hydrogen bond Heterocycle spiro[indoline-3 3′-indolizine] stereochemistry DAS Nuclear magnetic resonance spectroscopy Condensed Matter Physics Molecular conformation QD Chemistry Research Papers Crystallography chemistry Indoline supramolecular assembly Indolizine reaction mechanism heterocycle |
| Zdroj: | Acta Crystallographica. Section C, Structural Chemistry |
| ISSN: | 2053-2296 |
| Popis: | New spiro[indoline-3,3′-indolizine]s have been synthesized with high regio- and stereospecificity from simple starting materials in a one-step process. Different combinations of hydrogen bonds link the molecules to form either sheets or chains of rings. Five new spiro[indoline-3,3′-indolizine]s have been synthesized with high regio- and stereospecificity in one-pot three-component reactions between a substituted indole-2,3-dione, (S)-pipecolic acid and trans-3-benzoylacrylic acid, and subsequently characterized using a combination of elemental analysis, IR and 1H and 13C NMR spectroscopy, mass spectrometry and crystal structure analysis. (1′SR,2′SR,3RS,8a′RS)-2′-Benzoyl-5-fluoro-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C23H21FN2O4, (I), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H24N2O4, (II), are isomorphous, as are (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H24N2O4, (III), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-chloro-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C24H23ClN2O4, (IV). Within each isomorphous pair, the spiro ring systems show some conformational differences. In each of (I) and (II), the molecules are linked into complex sheets by a combination of four types of hydrogen bond, and in each of (III) and (IV), a combination of O—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules to form a chain of centrosymmetric rings. In (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-hexyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexahydro-2′H-spiro[indoline-3,3′-indolizine]-1′-carboxylic acid, C29H34N2O4, (V), a combination of five hydrogen bonds links the molecules into sheets of alternating R 2 2(16) and R 6 6(46) rings. A mechanism is proposed for the formation of compounds (I)–(V) and some comparisons with related structures are made. |
| Databáze: | OpenAIRE |
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