- Competing Regiochemical Pathways in the Heck Arylation of 1,2-Dihydronaphthalene
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The Heck reaction of aryl iodides with 1,2-dihydronaphthalene has been examined. Two separate reaction pathways are observed under all the conditions tried. Arylation adjacent to the aromatic ring leads to a subsequent double bond shift such that the product is a 1-aryl-1,2-dihydronaphthalene. The alternative regiochemistry leads to production of the corresponding 3-aryl-1,2-dihydronaphthalene, and labelling studies with specifically deuterated alkenes demonstrate that this is most likely to be the result of a trans Pd-H elimination pathway. The ratio always varies between 75:25 in favour of the 3-aryl product (Jeffery conditions) to 70:30 in favour of the 1-aryl product.
- Maeda, Kenji,Farrington, Edward J.,Galardon, Erwan,John, Benjamin D.,Brown, John M.
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- Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N- methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors
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The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activi
- Shao, Liming,Wang, Fengjiang,Malcolm, Scott C.,Ma, Jianguo,Hewitt, Michael C.,Campbell, Una C.,Bush, Larry R.,Spicer, Nancy A.,Engel, Sharon R.,Saraswat, Lakshmi D.,Hardy, Larry W.,Koch, Patrick,Schreiber, Rudy,Spear, Kerry L.,Varney, Mark A.
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p. 663 - 676
(2011/03/17)
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- Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: A diastereoselective total synthesis of (±)-indatraline
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Equation presented A new approach for the synthesis of (±)- indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by Phl(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.
- Silva Jr., Luiz F.,Siqueira, Fernanda A.,Pedrozo, Eliane C.,Vieira, Fabiana Y. M.,Doriguetto, Antonio C.
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p. 1433 - 1436
(2008/02/02)
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