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Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diaza-penta-cyclo[5.5.5.0(1,16).0(2,6).0(8,12)]hepta-deca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate.

Noland WE, Kroll NJ, Huisenga MP, Yue RA, Lang SB, Klein ND, Tritch KJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene.Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center.In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

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Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

No MeSH data available.


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Synthesis of the title compound (3). Structures (4)–(6) were the expected products.
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fig2: Synthesis of the title compound (3). Structures (4)–(6) were the expected products.

Mentions: Diels–Alder methodology: Reactions between vinyl­heterocycles and dienophiles have been useful in natural product synthesis and in the development of potential medicinal compounds (Booth et al., 2005 ▶; Kanai et al., 2005 ▶). Reported heterocycles include indole, pyrrole (Le Strat et al., 2005 ▶; Noland et al., 2013 ▶), furan (Brewer et al., 1971 ▶; Brewer & Elix, 1975b ▶; Davidson & Elix, 1970 ▶), benzo­furan, and benzo­thio­phene (Marrocchi et al., 2001 ▶; Pihera et al., 1999 ▶). A Diels–Alder reaction was attempted between 2-(α-styr­yl)thio­phene (1) (Tasch et al., 2013 ▶) and N-phenyl­male­imide (2) in an effort to expand this methodology (Fig. 2 ▶). Based on work by Watson (2012 ▶), the expected products were adduct (4), aromatized adduct (5), or (6) via ene addition of (2) to (4). Given the scope of simpler products from these reactions, it was surprising to obtain tetrone (3) in such a high yield.


Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diaza-penta-cyclo[5.5.5.0(1,16).0(2,6).0(8,12)]hepta-deca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate.

Noland WE, Kroll NJ, Huisenga MP, Yue RA, Lang SB, Klein ND, Tritch KJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Synthesis of the title compound (3). Structures (4)–(6) were the expected products.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257460&req=5

fig2: Synthesis of the title compound (3). Structures (4)–(6) were the expected products.
Mentions: Diels–Alder methodology: Reactions between vinyl­heterocycles and dienophiles have been useful in natural product synthesis and in the development of potential medicinal compounds (Booth et al., 2005 ▶; Kanai et al., 2005 ▶). Reported heterocycles include indole, pyrrole (Le Strat et al., 2005 ▶; Noland et al., 2013 ▶), furan (Brewer et al., 1971 ▶; Brewer & Elix, 1975b ▶; Davidson & Elix, 1970 ▶), benzo­furan, and benzo­thio­phene (Marrocchi et al., 2001 ▶; Pihera et al., 1999 ▶). A Diels–Alder reaction was attempted between 2-(α-styr­yl)thio­phene (1) (Tasch et al., 2013 ▶) and N-phenyl­male­imide (2) in an effort to expand this methodology (Fig. 2 ▶). Based on work by Watson (2012 ▶), the expected products were adduct (4), aromatized adduct (5), or (6) via ene addition of (2) to (4). Given the scope of simpler products from these reactions, it was surprising to obtain tetrone (3) in such a high yield.

Bottom Line: The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene.Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center.In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].

No MeSH data available.


Related in: MedlinePlus