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IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids

The title compounds C(24)H(21)NO(3)S, I, and C(24)H(21)NO(4), II, are the products of the IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines. Their mol­ecular structures comprise fused tricyclic systems containing thio­phene, cyclo­hexene and pyrrolidine rings (I) or fur...

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Autores principales: Toze, Flavien A. A., Nadirova, Maryana A., Mertsalov, Dmitriy F., Sokolova, Julya S., Dorovatovskii, Pavel V., Khrustalev, Victor N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176451/
https://www.ncbi.nlm.nih.gov/pubmed/30319788
http://dx.doi.org/10.1107/S2056989018012239
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author Toze, Flavien A. A.
Nadirova, Maryana A.
Mertsalov, Dmitriy F.
Sokolova, Julya S.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_facet Toze, Flavien A. A.
Nadirova, Maryana A.
Mertsalov, Dmitriy F.
Sokolova, Julya S.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
author_sort Toze, Flavien A. A.
collection PubMed
description The title compounds C(24)H(21)NO(3)S, I, and C(24)H(21)NO(4), II, are the products of the IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines. Their mol­ecular structures comprise fused tricyclic systems containing thio­phene, cyclo­hexene and pyrrolidine rings (I) or furan, cyclo­hexene and pyrrolidine rings (II). The central cyclo­hexene and pyrrolidine rings in both compounds adopt slightly twisted boat and envelope conformations, respectively. The dihedral angles between the basal plane of the pyrrolidine ring and the thio­phene (in I) or furan (in II) ring plane are 22.74 (16) and 26.29 (5)°, respectively. The nitro­gen atom both in I and II has practically planar environment [the sums of the bond angles are 359.8 and 358.9°, respectively]. In the crystal of I, the mol­ecules form hydrogen-bonded zigzag chains along [010] through strong inter­molecular O—H⋯O hydrogen bonds involving carb­oxy­lic and keto groups, whereas in the crystal of II, the mol­ecules are joined into centrosymmetric dimers by strong O—H⋯O hydrogen bonds between the carb­oxy­lic groups. In II, the atoms involved into these hydrogen bonds (and hence the whole carb­oxy­lic group) are disordered over two sets of sites with an occupancy ratio of 0.6:0.4. Compounds I and II crystallize as racemates consisting of enanti­omeric pairs of the 3aSR,4RS,4aRS,7aSR and 3aSR,4SR,4aRS,7aSR diastereomers, respectively.
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spelling pubmed-61764512018-10-12 IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids Toze, Flavien A. A. Nadirova, Maryana A. Mertsalov, Dmitriy F. Sokolova, Julya S. Dorovatovskii, Pavel V. Khrustalev, Victor N. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds C(24)H(21)NO(3)S, I, and C(24)H(21)NO(4), II, are the products of the IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines. Their mol­ecular structures comprise fused tricyclic systems containing thio­phene, cyclo­hexene and pyrrolidine rings (I) or furan, cyclo­hexene and pyrrolidine rings (II). The central cyclo­hexene and pyrrolidine rings in both compounds adopt slightly twisted boat and envelope conformations, respectively. The dihedral angles between the basal plane of the pyrrolidine ring and the thio­phene (in I) or furan (in II) ring plane are 22.74 (16) and 26.29 (5)°, respectively. The nitro­gen atom both in I and II has practically planar environment [the sums of the bond angles are 359.8 and 358.9°, respectively]. In the crystal of I, the mol­ecules form hydrogen-bonded zigzag chains along [010] through strong inter­molecular O—H⋯O hydrogen bonds involving carb­oxy­lic and keto groups, whereas in the crystal of II, the mol­ecules are joined into centrosymmetric dimers by strong O—H⋯O hydrogen bonds between the carb­oxy­lic groups. In II, the atoms involved into these hydrogen bonds (and hence the whole carb­oxy­lic group) are disordered over two sets of sites with an occupancy ratio of 0.6:0.4. Compounds I and II crystallize as racemates consisting of enanti­omeric pairs of the 3aSR,4RS,4aRS,7aSR and 3aSR,4SR,4aRS,7aSR diastereomers, respectively. International Union of Crystallography 2018-09-07 /pmc/articles/PMC6176451/ /pubmed/30319788 http://dx.doi.org/10.1107/S2056989018012239 Text en © Toze et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Toze, Flavien A. A.
Nadirova, Maryana A.
Mertsalov, Dmitriy F.
Sokolova, Julya S.
Dorovatovskii, Pavel V.
Khrustalev, Victor N.
IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title_full IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title_fullStr IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title_full_unstemmed IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title_short IMDAV reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
title_sort imdav reaction between phenyl­maleic anhydride and thien­yl(fur­yl)allyl­amines: synthesis and mol­ecular structure of (3asr,4rs,4ars,7asr)-5-oxothieno- and (3asr,4sr,4ars,7asr)-5-oxofuro[2,3-f]iso­indole-4-carb­oxy­lic acids
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176451/
https://www.ncbi.nlm.nih.gov/pubmed/30319788
http://dx.doi.org/10.1107/S2056989018012239
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