- Zinc-mediated acylation and sulfonation of pyrrole and its derivatives
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Pyrrole and its derivatives react smoothly with acid chlorides and sulfonyl chlorides in the presence of zinc metal in toluene at ambient temperature to afford the corresponding 2-acetyl and 2-sulfonyl pyrrole derivatives in high yields with high regioselectivity.
- Yadav,Reddy,Kondaji,Srinivasa Rao,Praveen Kumar
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Read Online
- Rapid access to 3-acyl indoles using ethyl acetate/triflic acid couple as the acylium donor and Cu(OAc)2catalysed aerial oxidation of indole benzoins
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Esters are potential acyl donors but are relatively unexplored for that purpose. A facile installation of acyl groups at the C-3 position of indoles under triflic acid catalysed conditions with easily available and cheap esters as new acylating agents is described herein. Furthermore, heterocycles like N-protected pyrrole, furan and thiophene were also suitable substrates for similar C-2 acylation. Analogous C-3 benzoylated products of indole were obtained, albeit in lower yields, by using methyl benzoate as a benzoyl donor. The benzoylated products were synthesised in much better yields via a copper(ii) catalysed aerial oxidation of indole containing benzoins. This journal is
- Talukdar, Ranadeep
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supporting information
p. 8876 - 8880
(2020/11/23)
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- 4-carbonyl-2-butene acid compound and use thereof
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The invention provides a 4-carbonyl-2-butene acid compound with good inhibition activity against PA_N. The compound has a general formula (I), wherein R1 represents C1-C4 alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl; and R2 represents hydroxy or substituted amino. The invention also relates to a medicine composition with the compound as an active component, and an application of the compound and the medicine composition provided by the invention in treating influenza.
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Paragraph 0052-0053
(2016/10/27)
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- Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines
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Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.
- Giles, Robert G.,Heaney, Harry,Plater, M. John
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p. 7367 - 7385
(2015/08/24)
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- Selective rhodium(III)-catalyzed cross-dehydrogenative coupling of furan and thiophene derivatives
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A hot couple: An unprecedented rhodium(III)-catalyzed cross-dehydrogenative coupling (CDC) of various furan and thiophene derivatives leads to valuable 2,2'-bi(heteroaryl) products in good yields and selectivities (see scheme). In addition, pyrroles and indoles can also be used as coupling partners, giving C3-arylated products. Copyright
- Kuhl, Nadine,Hopkinson, Matthew N.,Glorius, Frank
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supporting information; experimental part
p. 8230 - 8234
(2012/09/08)
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- Flash vacuum pyrolysis of 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2-vinyl-1H-pyrroles
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The flash vacuum pyrolysis of new 1,1-dimethyl- and 1-methyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides gave penta-substituted 2-vinyl-1H-pyrroles via sigmatropic [1,8]-H shift of the corresponding azafulvenium methide intermediates. In some cases these 1H-pyrroles underwent rearrangement to 2-allyl-1H-pyrroles. Di-substituted 2-vinylpyrroles have also been prepared and their reactivity studied. Under FVP N-benzyl-pyrrol-2-ylpropenoates were converted into 3H-pyrrolizin-3-ones. On the other hand, microwave-assisted reaction of 1-benzyl-2-vinyl-1H-pyrrole gave a 4,5,6,7-tetrahydro-1H-indole derivative.
- Soares, Maria I.L.,Lopes, Susana M.M.,Cruz, Pedro F.,Brito, Rui M.M.,Pinho e Melo, Teresa M.V.D.
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p. 9745 - 9753
(2008/12/22)
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- Oxidative radical cyclization to pyrroles under reducing conditions. Reductive desulfonylation of α-sulfonylpyrroles with tri-n-butyltin hydride
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1-(2-Bromobenzyl)-2-alkanesulfonylpyrroles (1c, 1d) and 1-(4-bromobutyl)-2-methylsulfonylpyrrols (8) undergo oxidative radical cyclization with partial or complete reductive desulfonylation to the pyrrolizidine derivatives 5 and 9 by an AIBN initiated reaction with tri-n-butyltin hydride.These cyclizations are suggested to proceed via a pseudo SRN1 process involving radical addition to the α position of the pyrrole nucleus not bearing the sulfonyl group.Reductive removal of the alkylsulfonyl moiety is proposed to occur in a second process after completion of the oxidative radical cyclization.The site of the radical addition is supported by deuterium labelling studies.Consistent with the timing of the loss of the sulfonyl group is that 2-alkylsulfonylpyrroles 11 are reductively desulfonylated under the same conditions that effect the oxidative radical cyclizations.
- Antonio, Yulia,Cruz, Ma. Elizabeth De La,Galeazzi, Edvige,Guzman, Angel,Bray, Brian L.,et al.
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