113-00-8Relevant articles and documents
Decomposition of 1-(ω-aminoalkanoyl)guanidines under alkaline conditions
Brennauer, Albert,Keller, Max,Freund, Matthias,Bernhardt, Günther,Buschauer, Armin
, p. 6996 - 6999 (2007)
The decomposition of some NG-(ω-aminoalkanoyl)argininamides, which are key intermediates for the preparation of radiolabeled and fluorescent neuropeptide Y receptor ligands, prompted us to synthesize a small series of simple 1-(ω-aminoalkanoyl)guanidines, and to investigate these model compounds for stability in alkaline buffers. The degradation of acylguanidines was monitored by time resolved UV spectroscopy. The most labile compound, 1-(5-aminopentanoyl)guanidine, decomposed with a half life of 19 s to yield piperidin-2-one (pH 10.4 at 25 °C). In contrast the half life of 1-(6-aminohexanoyl)guanidine is 7.7 h, which is comparable to the hydrolysis of acetylguanidine (t1/2 = 9.6 h) in alkaline solution.
Total synthesis of (±)-batzelladine K: A biomimetic approach
Ahmed, Nafees,Brahmbhatt, Keyur G.,Singh, Inder Pal,Bhutani, Kamlesh K.
, p. 2567 - 2570 (2010)
Total synthesis of batzelladine K was achieved by a biomimetic approach. The key reactions involve two Wittig reactions of phosphoranes and aldehydes leading to an ,-unsaturated ketone, followed by a condensation with guanidine. The synthesis was accomplished in four steps with an overall yield of 12%. The relative stereochemistry of batzelladine K was established by NOE experiments and comparison with literature values. Georg Thieme Verlag Stuttgart - New York.
Preparation and Properties of Substituted 1,6-Dihydro-1,3,5-triazin-2,4-diamines, 1',5',6',7'-Tetrahydrospiro-2'(3'H)-imines and 6-Phenyl-2,4-pyrimidindiamine
Wendelin, Winfried,Zmoelnig, Ilse,Schramm, Hans-Wolfgang
, p. 1189 - 1202 (1980)
Guanidine reacts with cyclohexanone, cycloheptanone, acetone and 3-pentanone, resp., in a molar ratio 2:1 to give the 1,3,5-triazaspiroundeca- and dodeca-1,3-dien-2,4-diamines 3a and 3b resp. and the 6,6-dimethyl- resp. diethyl-1,6-dihydro-1,3,5-triazin-2,4-diamines 3d and 3e resp.On the contrary, action of guanidine on cyclpentanone yields not 3c, but the 1',5',6',7'-tetrahydrospiro-2'(3'H)-imines 2c, 5c and 6c resp., which are 1:2- and 1:3-condensates.Phenylacetone is transformed by guanidine (1:2) to give 6-phenyl-2,4-pyrimidindiamine (8f).The structure of the compounds cited is proved by NMR-, IR-, and (partially) mass spectra.The different courses of the formation of 3a, b, d, e, 2c, 5c and 6c resp. and 8f are also discussed.The structural formulae of some additional bases, which were synthesized from guanidine and cyclopentanone, 3-pentanone and phenylacetone resp. could not be established. - Keywords: Guanidine, reactions with ketones; Ketones, reactions with guanidine; 2,4-Pyrimidindiamine, 6-phenyl; Spiro-2'(3'H)-imine, 1',5',6',7'-tetrahydro; 1,3,5-Triazaspiroundeca- and dodeca-1,3-dien-2,4-diamine; 1,3,5-Triazine-2,4-diamines, 1,6-dihydro-6,6-dialkyl, and salts
Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation
Wang, Fei,Nishimoto, Yoshihiro,Yasuda, Makoto
supporting information, p. 20616 - 20621 (2021/11/23)
Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.
Tin (II) cluster compound, and preparation method and application thereof
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Paragraph 0019; 0021-0022; 0024-0025; 0027-0028; 0030-0031;, (2020/06/09)
The invention provides a tin (II) cluster compound, and a preparation method and application thereof. The preparation method for the tin (II) cluster compound comprises the following synthesis steps:dissolving lithium trimethylsilyl benzene (phenyl) amide with diethyl ether under the protection of nitrogen, adding dimethylamino nitrile under an acetone bath condition, and carrying out a reactionovernight to obtain a diethyl ether solution of PhNC(NMe2)NSiMe3(Li); then adding the diethyl ether solution of PhNC(NMe2)NSiMe3(Li) into a diethyl ether suspension of SnCl2 under an acetone bath condition, carrying out slow heating to room temperature, and carrying out a reaction overnight; and performing standing and filtering, concentrating the obtained filtrate under vacuum, conducting crystallizing at room temperature, and separating out colorless crystals so as to obtain the tin (II) cluster compound, wherein a molar ratio of the lithium trimethylsilyl benzene (phenyl) amide to the dimethylamino nitrile to the SnCl2 is 1: 1: 1. The compound disclosed by the invention can be used as a catalyst for catalyzing the addition of aniline and N,N'-diisopropylcarbodiimide to generate guanidine, and has relatively good application prospects.
Guanidyl luteolin-chrome (III) complex and preparation method thereof
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Paragraph 0013; 0016; 0017; 0022, (2019/10/17)
The invention discloses a guanidyl luteolin-chrome (III) complex and a preparation method thereof. Luteolin is taken as a raw material, and the guanidyl luteolin-chrome (III) complex is prepared by free radical reaction, nucleophilic substitution reaction and trivalent chromium complexation. The production process is simple, the cost is low, and the large-scale industrial production of the guanidyl luteolin-chrome (III) complex is facilitated.
Silica Metal Oxide Vesicles Catalyze Comprehensive Prebiotic Chemistry
Mattia Bizzarri, Bruno,Botta, Lorenzo,Pérez-Valverde, Maritza Iveth,Saladino, Raffaele,Di Mauro, Ernesto,García-Ruiz, Juan Manuel
, p. 8126 - 8132 (2018/05/29)
It has recently been demonstrated that mineral self-assembled structures catalyzing prebiotic chemical reactions may form in natural waters derived from serpentinization, a geological process widespread in the early stages of Earth-like planets. We have s
Hydrogen sulfide donor in organic salt form and preparation method thereof
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Paragraph 0026; 0027, (2017/12/09)
The invention provides a hydrogen sulfide donor in an organic salt form and a preparation method thereof. The hydrogen sulfide donor is a salt structure formed by organic compounds with an alkaline structure and hydrogen sulfide. The structure of the hydrogen sulfide donor is simple. The preparation method is simple and easy to perform. Moreover, hydrogen sulfide donors in different forms can be obtained according to the needs of development and research. After the hydrogen sulfide donor enters an organism, the process of degradation in the organism and hydrogen sulfide supply is simple, rapid, and effective, there is not any requirement on enzyme or other complicated condition, and thus the hydrogen sulfide donor has a wide application prospect and a great application value.
Facile alkali-assisted synthesis of g-C3N4 materials and their high-performance catalytic application in solvent-free cycloaddition of CO2 to epoxides
Xu, Jie,Shang, Jie-Kun,Jiang, Quan,Wang, Yue,Li, Yong-Xin
, p. 55382 - 55392 (2016/07/06)
A series of graphitic carbon nitride materials were synthesized using guanidine hydrochloride (GndCl) as a precursor with the aid of alkali treatment. The introduction of alkali successfully enabled GndCl to be transformed into g-C3N4 at much lower calcination temperatures (450-475 °C). The g-C3N4 samples synthesized under various conditions have been characterized by several techniques including XRD, FT-IR, UV-vis, 13C NMR, and XPS spectroscopy. The results confirmed that the alkali could effectively accelerate further condensation of melem-like fragments to g-C3N4. Meanwhile, a possible mechanism of alkali-assisted synthesis of g-C3N4 from GndCl has been proposed. In solvent-free catalytic cycloaddition of CO2 to propylene oxide to propylene carbonate (PC), g-C3N4-NaOH and g-C3N4-KOH materials demonstrated high and stable catalytic performances, affording PC yields of ca. 90% under optimized reaction conditions. Moreover, the activities were superior to those obtained over g-C3N4 prepared without alkali treatment. In addition, the catalytic activity along with preparation method for the present g-C3N4 has also been compared with other reported g-C3N4-based catalysts.
A Global Scale Scenario for Prebiotic Chemistry: Silica-Based Self-Assembled Mineral Structures and Formamide
Saladino, Raffaele,Botta, Giorgia,Bizzarri, Bruno Mattia,Di Mauro, Ernesto,Garcia Ruiz, Juan Manuel
, p. 2806 - 2811 (2016/06/01)
The pathway from simple abiotically made organic compounds to the molecular bricks of life, as we know it, is unknown. The most efficient geological abiotic route to organic compounds results from the aqueous dissolution of olivine, a reaction known as serpentinization (Sleep, N.H., et al. (2004) Proc. Natl. Acad. Sci. USA 101, 12818-12822). In addition to molecular hydrogen and a reducing environment, serpentinization reactions lead to high-pH alkaline brines that can become easily enriched in silica. Under these chemical conditions, the formation of self-assembled nanocrystalline mineral composites, namely silica/carbonate biomorphs and metal silicate hydrate (MSH) tubular membranes (silica gardens), is unavoidable (Kellermeier, M., et al. In Methods in Enzymology, Research Methods in Biomineralization Science (De Yoreo, J., Ed.) Vol. 532, pp 225-256, Academic Press, Burlington, MA). The osmotically driven membranous structures have remarkable catalytic properties that could be operating in the reducing organic-rich chemical pot in which they form. Among one-carbon compounds, formamide (NH2CHO) has been shown to trigger the formation of complex prebiotic molecules under mineral-driven catalytic conditions (Saladino, R., et al. (2001) Biorganic & Medicinal Chemistry, 9, 1249-1253), proton irradiation (Saladino, R., et al. (2015) Proc. Natl. Acad. Sci. USA, 112, 2746-2755), and laser-induced dielectric breakdown (Ferus, M., et al. (2015) Proc Natl Acad Sci USA, 112, 657-662). Here, we show that MSH membranes are catalysts for the condensation of NH2CHO, yielding prebiotically relevant compounds, including carboxylic acids, amino acids, and nucleobases. Membranes formed by the reaction of alkaline (pH 12) sodium silicate solutions with MgSO4 and Fe2(SO4)3·9H2O show the highest efficiency, while reactions with CuCl2·2H2O, ZnCl2, FeCl2·4H2O, and MnCl2·4H2O showed lower reactivities. The collections of compounds forming inside and outside the tubular membrane are clearly specific, demonstrating that the mineral self-assembled membranes at the same time create space compartmentalization and selective catalysis of the synthesis of relevant compounds. Rather than requiring odd local conditions, the prebiotic organic chemistry scenario for the origin of life appears to be common at a universal scale and, most probably, earlier than ever thought for our planet.
