- Asymmetric Cross [10+2] Cycloadditions of 2-Alkylidene-1-indanones and Activated Alkenes under Phase-Transfer Catalysis
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Isobenzofulvene species are versatile synthons in organic chemistry, which have been employed in diverse challenging higher-order cycloaddition reactions. Here, the first chemoselective and asymmetric cross [10+2] cycloaddition reaction between activated 2-alkylidene-1-indanones and a variety of electron-deficient alkenes has been developed, relying on the in situ generation of dearomative 1-hydroxyl isobenzofulvene anion intermediates under the catalysis of a newly designed bulky cinchona-derived phase-transfer compound. An array of fused frameworks with multifunctionalities were generally furnished in excellent diastereo- and enantioselectivity, even at 1 mol % catalyst loadings.
- Yang, Yang,Jiang, Ying,Du, Wei,Chen, Ying-Chun
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supporting information
p. 1754 - 1758
(2020/02/11)
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- Nucleophilic Nitration of Arynes by Sodium Nitrite and its Multicomponent Reaction Leading to Double-Functionalized Arenes
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An unusual nucleophilic nitration of arynes by NaNO2 in the presence of water has been developed, and the concept was further demonstrated to accomplish a double functionalization of arynes using a multicomponent reaction protocol to synthesize pharmaceutically important (2-nitrophenyl)methanol derivatives. Such substitution ortho to -NO2 is difficult by other means. The reaction conditions are mild and avoid the use of strong acids, expensive transition metal catalysts, and additives.
- Dhokale, Ranjeet A.,Mhaske, Santosh B.
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supporting information
p. 3010 - 3013
(2016/07/06)
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- Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability
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A lead optimization campaign in our previously reported sulfamoyl benzamide class of CB2 agonists was conducted to improve the in vitro metabolic stability profile in this series while retaining high potency and selectivity for the CB2 receptor. From this study, compound 14, N-(3,4-dimethyl-5-(morpholinosulfonyl)phenyl)-2,2-dimethylbutanamide, was identified as a potent and selective CB2 agonist exhibiting moderate in vitro metabolic stability and oral bioavailability. Compound 14 demonstrated in vivo efficacy in a rat model of post-surgical pain.
- Sellitto, Ian,Bourdonnec, Bertrand Le,Worm, Karin,Goodman, Allan,Savolainen, Markku A.,Chu, Guo-Hua,Ajello, Christopher W.,Saeui, Christopher T.,Leister, Lara K.,Cassel, Joel A.,DeHaven, Robert N.,LaBuda, Christopher J.,Koblish, Michael,Little, Patrick J.,Brogdon, Bernice L.,Smith, Steven A.,Dolle, Roland E.
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scheme or table
p. 387 - 391
(2010/04/06)
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- 4-and 5-nitroindane
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Mononitration of indane produces a mixture of 4- and 5- nitroindanes. Crystallization from mixtures occurs after distillation improves composition of a major component to above 80%. 4-Nitroindane: triclinic, space group P1 (#2), a = 7.332(4) A, b = 8.304(4) A, c = 8.358(4) A, α = 61.43(4)°, β = 67.60(4)°, γ = 70.15(4)°, V = 405.4(4) A3, Z = 2. Non-H-atoms are nearly planar, aliphatic H's are eclipsed. 5-Nitroindane: monoclinic, space group P21/c (#14), a = 10.946(8) A, b = 15.643(10) A, c = 9.415(6) A, β = 92.34(5)°, V = 1611(2) A3, Z = 8. Non-H-atoms in the two molecules differ in torsion of the nitro group with respect to indane and fold of the nonbenzylic methylene group. Semiempirical calculations (PM3) suggest that distorsion from planarity may be associated with the two lowest energy vibrational modes. Uv, ir, ms, proton, and 13C-nmr spectra are correlated with the solid state structures.
- Fuller, Jason F.,Valente, Edward J.
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p. 815 - 821
(2007/10/03)
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