- Aromatic sulfonyl hydrazides and sulfonyl hydrazones: Antimicrobial activity and physical properties
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A series of novel aromatic sulfonamide derivatives (1-7) were synthesized and characterized by elemental analyses, FT-IR, 1H NMR, 13C NMR, and LC/MS techniques. The compounds' quantum mechanical descriptors, surface area, and molecul
- Aslan, H. Guezin,Karacan, Nurcan
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p. 1330 - 1338
(2013/05/09)
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- The antibacterial activity of some sulfonamides and sulfonyl hydrazones, and 2D-QSAR study of a series of sulfonyl hydrazones
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Benzenesulfonicacid-1-methylhydrazide (1) and its four aromatic sulfonyl hydrazone derivatives (1a-1d), N-(3-amino-2-hydroxypropyl)benzene sulfonamide (2) and N-(2-hydroxyethyl)benzenesulfonamide (3) were synthesized and their structures were determined b
- Aslan, H. Guezin,Oezcan, Servet,Karacan, Nurcan
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p. 329 - 336,8
(2012/12/12)
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- Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles
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The 1,3-dipolar cycloaddition reactions of various N-tethered alkenyl aldehydes with some cyclic and acyclic amino acids have been studied. Some key sulfonamides having strategically positioned aldehyde and olefinic tether have been synthesized and effectively subjected to intramolecular azomethine ylide cycloaddition reaction resulting in a series of pyrrolo[3,4-b]pyrrole and its N-1-C-2 derivatives, and a series of novel heterotricyclic compounds, perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles, in good yields. The intramolecular cycloaddition reaction was found to be highly stereoselective to form only cis-fused cycloadducts in all cases.
- Poornachandran, Mahalingam,Raghunathan, Raghavachary
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p. 6461 - 6474
(2008/09/21)
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- Regioselectivity and the nature of the reaction mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with primary amines
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Second-order rate constants have been measured for the reaction of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of primary amines. The nucleophilic substitution reaction proceeds through competitive S-O and C-O bond fission pathways. The S-O bond fission occurs dominantly for reactions with highly basic amines or with substrates having a strong electron-withdrawing group in the sulfonyl moiety. On the other hand, the C-O bond fission occurs considerably for the reactions with low basic amines or with substrates having a strong electron-donating group in the sulfonyl moiety, emphasizing that the regioselectivity is governed by both the amine basicity and the electronic effect of the sulfonyl substituent X. The apparent second-order rate constants for the S-O bond fission have resulted in a nonlinear Bronsted-type plot for the reaction of 2,4-dinitrophenyl benzenesulfonate with 10 different primary amines, suggesting that a change in the rate-determining step occurs upon changing the amine basicity. The microscopic rate constants (k1 and k2/k-1 ratio) associated with the S-O bond fission pathway support the proposed mechanism. The second-order rate constants for the S-O bond fission result in good linear Yukawa-Tsuno plots for the aminolyses of 2,4-dinitrophenyl X-substituted benzenesulfonates. However, the second-order rate constants for the C-O bond fission show no correlation with the electronic nature of the sulfonyl substituent X, indicating that the C-O bond fission proceeds through an SNAR mechanism in which the leaving group departure occurs rapidly after the rate-determining step.
- Um, Ik-Hwan,Hong, Jin-Young,Kim, Jung-Joo,Chae, Ok-Mi,Bae, Sun-Kun
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p. 5180 - 5185
(2007/10/03)
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- Metal oxide in aqueous organic solution promoted chemoselective N-sulfonylation of hydrophilic amino alcohols
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The reaction of hydrophilic amino alcohols with sulfonyl chlorides in the presence of metal oxide (MgO, CuO, Ag2O) in aqueous organic solution cleanly provided alkanolsulfonamide. Advantages of this method were mild, neutral reaction conditions
- Kang, Hak Hee,Rho, Ho Sik,Kim, Duck Hee,Oh, Seong-Geun
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p. 7225 - 7227
(2007/10/03)
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