- Leaving group and regioselectivity switches in the aminoalkylation reaction of indoles and related heterocycles with α-amido sulfones
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The regioselective aminoalkylation of indoles and related heterocycles with α-amido sulfones under basic conditions has been studied. The reaction that employed the MeMgBr/MgBr2 system provided high yields of 3-(1-carbamoylalkyl)indoles. On the other hand, the reaction that used Cs 2CO3 afforded 1-(1-carbamoylalkyl)indoles exclusively in high yields. The first reaction constitutes a switch of the leaving group of the α-amido sulfone in comparison to previously reported reactions between indoles and α-amido sulfones, which provided 3-(1-arylsulfonylalkyl) indoles. The second reaction constitutes a switch in the regioselectivity. The extensions of these C- and N-aminoalkylations starting from pyrroles and 7-azaindole have also been studied. Structurally diverse aminoalkylated indoles, pyrroles, and 7-azaindoles were obtained with excellent yield in most of the cases. The regioselective aminoalkylation of indoles and heterocycles with α-amido sulfones under basic conditions is described. The reaction with MeMgBr/MgBr2 gives 3-(1-carbamoylalkyl)indoles, whereas employing Cs2CO3 yields 1-(1-carbamoylalkyl)indoles. The first case presents a switch of the leaving group of the α-amido sulfone, whereas the second demonstrates a switch in the regioselectivity. Copyright
- Blay, Gonzalo,Giron, Rosa M.,Montesinos-Magraner, Marc,Pedro, Jose R.
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supporting information
p. 3885 - 3895
(2013/07/19)
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- Regioselective arylations of α-amido sulfones with electron-rich arenes through friedel-crafts alkylations catalyzed by ferric chloride hexahydrate: Synthesis of unsymmetrical and bis-symmetrical triarylmethanes
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Ferric chloride hexahydrate is a highly efficient catalyst for the regioselective arylation of α-amido sulfones. The products undergo further Friedel-Crafts alkylations with heteroaromatic or electron-rich arenes to afford unsymmetrical or bis-symmetrical
- Thirupathi, Ponnaboina,Kim, Sung Soo
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supporting information; experimental part
p. 1798 - 1808
(2010/06/15)
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- A mild and efficient catalytic mannich-type reaction as a simple access to N -benzyloxycarbonyl -amino ketones
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N-Benzyloxycarbonylamino sulfones react with aromatic ketones in the presence of catalytic amount of boron trifluoride-diethyl ether at room temperature to afford the corresponding protected β-amino ketones in high yields (71-87%). Georg Thieme Verlag Stu
- Das, Biswanath,Reddy, Gandolla Chinna,Balasubramanyam, Penagaluri,Veeranjaneyulu, Boyapati
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scheme or table
p. 2057 - 2062
(2010/08/13)
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- Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxycarbonylamino p-tolylsulfones with allyltrimethylsilane: Synthesis of protected homoallylic amines
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Indium triflate-catalyzed allylation reactions of N-sulfonyl aldimines or N-alkoxyloxycarbonylamino p-tolylsulfone with allyltrimethylsilane have been successfully developed to produce protected homoallylic amines.
- Thirupathi, Ponnaboina,Kim, Sung Soo
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scheme or table
p. 8623 - 8628
(2010/11/18)
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- InBr3: A versatile catalyst for the different types of Friedel-Crafts reactions
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(Chemical Equation Presented) Mild and efficient InBr3-catalyzed Friedel-Crafts alkylation of heteroaromatic or electron-rich aromatic compounds with α-amido sulfones at room temperature in CH2Cl2 has been developed. The p
- Thirupathi, Ponnaboina,Sung, Soo Kim
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supporting information; experimental part
p. 7755 - 7761
(2009/12/27)
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- Configurational stability of chiral, nonconjugated nitrogen-substituted organolithium compounds generated by tin-lithium exchange of N-[(1-Tri-n-butylstannyl)alkyl]imidazolidin-2-ones and -oxazolidin-2-ones
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Chiral, nonracemic, nonconjugated, acyclic nitrogen-substituted organolithium compounds were generated in order to study the configurational stability of such species. The organolithium compounds were generated by tin-lithium exchange on N-[(1-tri-n-butyl
- Pearson, William H.,Lindbeck, Aline C.,Kampf, Jeff W.
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p. 2622 - 2633
(2007/10/02)
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