- Biomimetic alloxan-catalyzed intramolecular redox reaction with O2: One-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles
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Given the necessity of sacrificial reductants in various biomimetic aerobic oxygenations, alloxan-catalyzed aerobic redox system for one-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles was developed by ingeniously binding both the substrate sulfide and sacrificial reductant. This mild and transition-metal-free protocol undergoes two oxidations without additional sacrificial reagents, except for the environmentally benign molecular oxygen.
- Zhang, Shiqi,Yi, Dong,Li, Guangxun,Li, Ling,Zhao, Gang,Tang, Zhuo
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supporting information
(2020/12/25)
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- DEUTERATED DERIVATIVES OF 6,8-BIS(BENZYLSULFANYL)OCTANOIC ACID
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The invention provides new deuterated derivatives of 6,8-bis(benzylsulfanyl)octanoic acid, pharmaceutical compositions thereof, and methods for treating cancer with the new compositions.
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Paragraph 0083
(2021/02/12)
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- Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines
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The first systematic study of simple nitronate nucleophiles in iridium-catalyzed allylic alkylation is described. Using a tol-BINAP-modified π-allyliridiumC,O-benzoate catalyst, α,α-disubstituted nitronates substitute racemic branched alkyl-substituted al
- Jung, Woo-Ok,Mai, Binh Khanh,Spinello, Brian J.,Dubey, Zachary J.,Kim, Seung Wook,Stivala, Craig E.,Zbieg, Jason R.,Liu, Peng,Krische, Michael J.
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supporting information
p. 9343 - 9349
(2021/07/19)
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- 1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS
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Compositions of the invention comprise 1,2-dithiolane, dithiol and related compounds useful as therapeutic agents for the treatment and prevention of diseases and conditions associated with aberrant EGFR activity.
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Paragraph 0316-0317
(2018/08/12)
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- 1,2-DITHIOLANE AND DITHIOL COMPOUNDS USEFUL IN TREATING MUTANT EGFR-MEDIATED DISEASES AND CONDITIONS
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Compositions of the invention comprise 1,2-dithiolane, dithiol and related compounds useful as therapeutic agents for the treatment and prevention of diseases and conditions associated with aberrant EGFR activity.
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Paragraph 0253; 0254
(2018/08/09)
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- Enantioselective Radical Cyclization for Construction of 5-Membered Ring Structures by Metalloradical C-H Alkylation
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Radical cyclization represents a powerful strategy for construction of ring structures. Traditional radical cyclization, which is based on radical addition as the key step, necessitates the use of unsaturated substrates. Guided by the concept of metalloradical catalysis, a different mode of radical cyclization that can employ saturated C-H substrates is demonstrated through the development of a Co(II)-based system for catalytic activation of aliphatic diazo compounds for enantioselective radical alkylation of various C(sp3)-H bonds. It allows for efficient construction of chiral pyrrolidines and other valuable 5-membered cyclic compounds. This alternative strategy of radical cyclization provides a new retrosynthetic paradigm to prepare five-membered cyclic molecules from readily available open-chain aldehydes through the union of C-H and C=O elements for C-C bond formation.
- Wang, Yong,Wen, Xin,Cui, Xin,Zhang, X. Peter
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supporting information
p. 4792 - 4796
(2018/04/17)
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- The synthesis of phosphonic acids derived from homocysteine via transesterification reactions
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An efficient methodology for the synthesis of S-substituted derivatives of phosphonohomocysteine has been developed. It starts from the corresponding thiols and is based on a synthetic sequence consisting of (i) the Kabachnik-Fields reaction, (ii) the tra
- Picha, Jan,Budesinsky, Milos,Fiedler, Pavel,Jiracek, Jiri
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experimental part
p. 80 - 99
(2012/03/09)
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- One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction
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Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys-Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2,2,2-Trifluoroethanol was shown to be a superior reaction media than methanol in some reactions. Also, the 4-methyl-2,6,7-trioxabicyclo[2.2.2]octyl derivative (OBO-ester) of isocyanoacetic acid was shown to be superior to use than ethyl isocyanoacetate as a peptide synthesis precursor in cases when higher reactivity of an isocyanide is required.
- Zhdanko, Alexander G.,Gulevich, Anton V.,Nenajdenko, Valentine G.
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experimental part
p. 4692 - 4702
(2009/10/02)
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- Synthesis of an oxa-lipoic acid
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The synthesis of an oxa-lipoic acid is reported here for the first time. We have achieved the synthesis of the title compound starting from commercially available acrolein using a Michael addition and Knoevenagel condensation as key reactions.
- Reddy, D. Srinivasa,Srinivas,Balasubrahmanyam,Iqbal, Javed
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p. 4533 - 4534
(2008/02/03)
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- Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids
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A new method for the synthesis of protected Nα-(ω-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino acids is reported. These new amino acids serve as building units for the synthesis of backbone-cyclic peptides. They are orthogonally protected at the α-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.
- Bitan, Gal,Muller, Dan,Kasher, Ron,Gluhov, Evgenia V.,Gilon, Chaim
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p. 1501 - 1510
(2007/10/03)
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- Regiochemical and Stereochemical Studies on Halocyclization Reactions of Unsaturated Sulfides
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The regiochemistry and stereochemistry for the halocyclization reactions of unsaturated benzyl sulfides have been examined as a function of tether length, type of unsaturation (carbon-carbon double bond versus carbon-carbon triple bond), substituents, and halogenating agent.Alkenyl sulfides were found to react with iodine or bromine at room temperature to give five-membered ring cycloadducts exclusively over those having four-membered rings, while for larger systems, six-membered ring products are formed preferentially over their five-membered ring isomers and exclusively over the seven-membered ring adducts.The endo- versus exo-regioselectivity of these alkenyl sulfide ring closure most likely reflects the difference in thermodynamic stabilities of the β-halo sulfide cycloadducts, which are able to equilibrate via a common episulfonium intermediate.The efficiency of cyclization process markedly drops off for these alkenyl sulfides as the tether length increases beyond four intervening carbon centers.Thus, while the halogenations of 3-butenyl sulfides and 4-pentenyl sulfides give high yields of cycloadducts, those of 5-hexenyl sulfides afford only small amounts of cyclized products and large quantities of acyclic dibromides.Conversely, the reactions of acetylenic sulfides with iodine give uniformly high yields and regiochemical control regardless of the tether length.Thus, 3-butynyl and 4-pentynyl sulfides cyclize cleanly to the five-membered ring while 5-hexynyl sulfides give exclusively the six-membered ring.The products arising from these alkynyl sulfide ring closures are believed to be formed under kinetic control.The methodology has been applied to the synthesis of unusual bicyclic β-lactams related to the penicillin family of antibiotics.
- Ren, Xiao-Feng,Turos, Edward,Lake, Charles H.,Churchill, Melvyn Rowen
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p. 6468 - 6483
(2007/10/03)
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- Synthesis and Biological Activity of 1,2-Dithiolanes and 1,2-Dithianes Bearing a Nitrogen-containing Substituent
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A series of 1,2-dithiolanes, 1,2-dithianes and related compounds bearing a nitrogen-containing substituent were synthesized and their pesticidal activity was tested.A new general synthetic route to 1,2-dithiolanes was established from 1,3-diols.A variation in the position and character of the nitrogen atom is shown to be allowable to some extent for promoting insecticidal activity, unlike the case of sulfur atoms.Most compounds showed acaricidal activity, the strongest being displayed by cis-3,5-bis(dimethylaminomethyl)-1,2-dithiolane.
- Uneme, Hideki,Mitsudera, Hiroyuki,Kamikado, Toshiya,Kono, Yoshiaki,Manabe, Yukiaki,Numata, Mitsuo
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p. 2023 - 2033
(2007/10/02)
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- An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide
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It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.
- Yamada, Hiroyuki,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
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p. 949 - 950
(2007/10/02)
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