4671-93-6Relevant academic research and scientific papers
Catalyst and Additive-Free Selective Ring-Opening Selenocyanation of Heterocycles with Elemental Selenium and TMSCN
Lu, Li-Guo,Bi, Kang,Huang, Xiao-Bo,Liu, Miao-Chang,Zhou, Yun-Bing,Wu, Hua-Yue
, p. 1346 - 1351 (2021)
A catalyst and additive-free strategy for selective ring-opening selenocyanation of saturated heterocycles with elemental selenium and TMSCN is developed, affording a series of aliphatic selenocyanates and selenaheterocycles. In the case of unprotected unstrained N-heterocycles, the reactions offer ammonium selenonitriles that prove to be an efficient selenonitrile reagent. (Figure presented.).
(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp3)-H Bonds
Yu, Fei,Li, Chuang,Wang, Chuangye,Zhang, Hongwei,Cao, Zhong-Yan
supporting information, p. 7156 - 7160 (2021/09/18)
A new, simple, yet easily accessible, (1-selenocyanatoethyl)benzene has been designed and applied as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp3)-H bonds for the first time. This protocol is featured with mild reaction conditions and wide substrate scope. Control experiments reveal that a radical-group transfer mechanism might be involved.
Solvent free nucleophilic selenocyanation with [bmim][SeCN]. Direct access to perfluoroalkylselenide compounds
De-Zordo Banliat, Arnaud,Grollier, Kévin,Damond, Aurélie,Billard, Thierry,Dagousset, Guillaume,Magnier, Emmanuel,Pégot, Bruce
, (2021/11/08)
Available online-1-n-butyl-3-methylimidazolium selenocyanate ([bmim][SeCN]) proved to be a very efficient reagent for selenocyanation of alkyl halides. As part of an eco-friendly process, no organic solvents were used during the transformation and reaction times are reduced by using microwave as a heating source. The ionic liquid was carefully recycled in two different ways. Selenocyanate compounds were successfully transformed into trifluoromethylselenides in a one-pot two step procedure.
AIBN-initiated direct thiocyanation of benzylic sp3C-H with: N -thiocyanatosaccharin
Wu, Di,Duan, Yongjie,Liang, Kun,Yin, Hongquan,Chen, Fu-Xue
supporting information, p. 9938 - 9941 (2021/10/12)
Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C-SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved the use of readily available raw materials and resulted in high product yields (up to 100%), both being great advantages for synthesizing benzyl thiocyanates.
Novel selenocyano reagent as well as preparation method and application thereof
-
Paragraph 0075-0077, (2021/03/13)
The invention discloses a novel selenocyano reagent, which has a structure as shown in a formula I. The selenocyano reagent is low in preparation cost, stable in property and easy to store, can be widely applied to selenocyanation reaction of various halogenated hydrocarbon compounds, is applied to preparation of selenocyanate, is mild and simple in reaction condition and easy to implement, and has relatively high selenocyanation efficiency.
Pronounced activity of aromatic selenocyanates against multidrug resistant ESKAPE bacteria
Nasim, Muhammad Jawad,Witek, Karolina,Kincses, Annamária,Abdin, Ahmad Yaman,?es?awska, Ewa,Mar?, Ma?gorzata Anna,Gajdács, Márió,Spengler, Gabriella,Nitek, Wojciech,Latacz, Gniewomir,Karczewska, El?bieta,Kie?-Kononowicz, Katarzyna,Handzlik, Jadwiga,Jacob, Claus
supporting information, p. 6021 - 6031 (2019/04/16)
Selenocyanates represent an interesting class of organic selenium compounds. Due to their similarity with better known natural (iso-)thiocyanates, they promise high biological activity and may also be metabolized to other Reactive Selenium Species (RSeS),
Potent anti-proliferative activities of organochalcogenocyanates towards breast cancer
Banerjee, Kaustav,Padmavathi, Ganesan,Bhattacherjee, Debojit,Saha, Suchismita,Kunnumakkara, Ajaikumar B.,Bhabak, Krishna P.
, p. 8769 - 8782 (2018/11/30)
The pharmacological importance, particularly the anti-cancer and chemopreventive potentials, of organochalcogen compounds has attracted wide research attention recently. Herein we describe the synthesis of a series of organochalcogenocyanates that have one or more selenocyanate or thiocyanate units in a single molecule. The anti-proliferative activity of these organochalcogenocyanates in different breast cancer cells shows that selenocyanates exhibit much higher anti-proliferative activities than thiocyanates in general. Our study reveals that the activity of benzyl selenocyanate (1, BSC) could be significantly enhanced by 4-nitro substitution (12), which was more selective towards triple-negative breast cancer cells (MDA-MB-231) over other ER+ breast cancer cells (MCF-7 and T-47D). Furthermore, to the best of our knowledge, this is the first report on the synthesis of compounds having more than two selenocyanate units with promising anti-proliferative activities. Our studies further indicate that the apoptotic activities of selenocyanates are associated with modulation of cellular morphology and cell cycle arrest at S-phase. Selenocyanates also inhibited cellular migration and exhibited weak antioxidant activities. An effective binding interaction of compound 12 with serum albumin indicates its feasible transport in the bloodstream for its enhanced anti-cancer properties. Mechanistic studies by western blot analysis demonstrate that benzylic selenocyanates exhibit anti-proliferative activities by modulating key cellular proteins such as Survivin, Bcl-2 and COX-2; this was further supported by molecular docking studies. The results of this study would be helpful in designing suitable chemotherapeutic and chemopreventive drugs in the future.
Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Eguaogie, Olga,Conlon, Patrick F.,Ravalico, Francesco,Sweet, Jamie S. T.,Elder, Thomas B.,Conway, Louis P.,Lennon, Marc E.,Hodgson, David R. W.,Vyle, Joseph S.
supporting information, p. 87 - 92 (2017/02/15)
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-e
Benzyltrifluoromethyl (or Fluoroalkyl) Selenide: Reagent for Electrophilic Trifluoromethyl (or Fluoroalkyl) Selenolation
Glenadel, Quentin,Ismalaj, Ermal,Billard, Thierry
, p. 8268 - 8275 (2016/09/28)
Trifluoromethylseleno substituent (CF3Se) is an emerging group, but its direct introduction onto organic molecules is still quite limited and mainly restricted to nucleophilic methods. Herein, we describe a new approach to easily and safely perform electrophilic trifluoromethylselenolation starting from a simple and easily accessible reagent, namely, benzyltrifluoromethyl selenide. This strategy can be generalized to various fluoroalkylselanyl groups, even functionalized ones.
Stereoselective synthesis of alkyl styryl selenides in one-pot: A straightforward approach by in situ dialkyl diselenide formation under transition metal-free conditions
Heredia, Adrián A.,Pe?é?ory, Alicia B.
, p. 105699 - 105706 (2015/12/26)
A simple procedure for the synthesis of alkyl styryl selenides was developed. This methodology involves the in situ generation of selenolate anions by a one-pot and three-step protocol where a nucleophilic substitution between KSeCN and alkyl halides affords the corresponding alkyl selenocyanate in the first step, giving dialkyl diselenide by a further K3PO4-assisted reaction. Subsequent reduction yields the alkyl selenolate anions which react with substituted (E,Z)-β-styryl halides to afford the corresponding vinyl selenides with retention of stereochemistry and from moderate to excellent yields. This procedure does not require a catalyst, proceeds under an air atmosphere and within a short reaction time, and is free from diselenide and malodorous and air-sensitive alkyl selenols as starting materials.
