Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

• Mio Matsumura,
• Kaho Tsukada,
• Kiwa Sugimoto,
• Yuki Murata and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

• with potential bioactivity, has been reported [4][5][6][7]. Similarly, organoselenium compounds have also received increased attention in recent years due to their promising applications as bioactive substances in drug discovery [8]. Among these compounds, alkynyl selenides have attracted interest in

• ]. However, there is no reported example of the synthesis of alkynyl imidazopyridinyl selenides. The Se–C bond-formation reaction using transition metals such as Pd, Ru, Ni, Fe, and Cu as catalysts is one of the most powerful synthetic tools for preparing organoselenium compounds [16][17][18]. Diselenides

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

• Mio Matsumura,
• Tsutomu Takahashi,
• Hikari Yamauchi,
• Shunsuke Sakuma,
• Yukako Hayashi,
• Tadashi Hyodo,
• Tohru Obata,
• Kentaro Yamaguchi,
• Yasuyuki Fujiwara and
• Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

• The synthesis of organoselenium compounds and their biological activity have attracted considerable attention in research fields directed to drug discovery [1][2][3][4][5][6][7][8][9][10][11][12][13]. Among these compounds, heteroaryl selenides and heteroaryl diselenides have been synthesized by a

• studies in the synthesis of organoselenium compounds containing imidazo[1,2-a]pyridine rings [27][28][29][30][31][32][33][34], the synthesis of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides by the Cu-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridines with Se powder is

Regio- and stereoselective synthesis of new ensembles of diversely functionalized 1,3-thiaselenol-2-ylmethyl selenides by a double rearrangement reaction

• Svetlana V. Amosova,
• Andrey A. Filippov,
• Nataliya A. Makhaeva,
• Alexander I. Albanov and
• Vladimir A. Potapov

Beilstein J. Org. Chem. 2020, 16, 515–523, doi:10.3762/bjoc.16.47

• -thiaselenole; nucleophilic addition; nucleophilic substitution; rearrangement; seleniranium intermediate; Introduction The regio- and stereoselective synthesis of organoselenium compounds based on selenium-centered electrophilic reagents has been one of the most important and effective directions in

• organoselenium chemistry for half a century [1][2][3][4][5][6][7][8][9][10][11][12]. The important trend in the field of organoselenium chemistry within the last 15 years was the involvement of selenium dihalides in the synthesis of organoselenium compounds [13][14]. The first synthesis of organoselenium

• compound from selenium dihalides was the preparation of 1,4-selenasilafulvenes by cyclization reaction with diethynyldimethylsilane [15][16]. The creation of new methodologies for the synthesis of new classes of organoselenium compounds and especially selenium heterocycles, with promising biological

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

• Gabriel P. Costa,
• Natália Seus,
• Juliano A. Roehrs,
• Raquel G. Jacob,
• Ricardo F. Schumacher,
• Thiago Barcellos,
• Rafael Luque and
• Diego Alves

Beilstein J. Org. Chem. 2017, 13, 694–702, doi:10.3762/bjoc.13.68

• ; organocatalysis; organoselenium compounds; sonochemistry; 1,2,3-triazoles; Introduction Substituted 1,2,3-triazoles are an interesting class of heterocyclic compounds distinguished by their biological activities [1][2][3] as well as in various fields of chemistry [4][5][6][7][8][9][10][11][12][13][14][15]. The

• 1,2,3-triazoles [33][34][35][36][37]. Selanyltriazoyl carboxylates, carboxamides, carbonitriles or sulfones were synthesized in good to excellent yields using catalytic amounts of an organocatalyst. Organoselenium compounds are attractive synthetic targets because of their selective reactions [38][39

O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside

• Roman Sommer,
• Dirk Hauck,
• Annabelle Varrot,
• Anne Imberty,
• Markus Künzler and
• Alexander Titz

Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282

• : carbohydrate chemistry; fucose; lectin; selenoglycoside; Introduction Since the discovery of seleno mercaptan by Siemens in 1847 [1], organoselenium compounds have attracted high attention. Besides their biological and pharmaceutical relevance, e.g., selenocysteine or ebselen [2][3][4][5], selenium-containing

Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

• Andrea Temperini,
• Massimo Curini,
• Ornelio Rosati and
• Lucio Minuti

Beilstein J. Org. Chem. 2014, 10, 1267–1271, doi:10.3762/bjoc.10.127

• tolerance. Moreover, the produced selenones could be useful intermediates for the synthesis of different heterocyclic compounds. Keywords: heterocycles; monoperoxyphthalate; oxidation; selenides; selenones; Introduction Organoselenium compounds have received considerable attention in recent times because

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

• Yohsuke Kobiki,
• Shin-ichi Kawaguchi,
• Takashi Ohe and
• Akiya Ogawa

Beilstein J. Org. Chem. 2013, 9, 1141–1147, doi:10.3762/bjoc.9.127

• absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method. Keywords: arylation; unsymmetrical diaryl selenide; free radical; organobismuth; photoinduced reaction; Introduction A number of organoselenium compounds are

Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation

• Vadim A. Soloshonok and
• Donna J. Nelson

Beilstein J. Org. Chem. 2011, 7, 744–758, doi:10.3762/bjoc.7.85

• straightforward and general methods for the preparation of the corresponding selenium derivatives, which are useful intermediates in organic synthesis, often with interesting biological applications [4][5]. Thus, organoselenium compounds are reported to have antitumor [6][7][8], antimicrobial [7][8], antiviral [7

• ][8], and anti-oxidant [9][10] properties. It is interesting to note that the current applications of organoselenium derivatives have outpaced those of conventional inorganic selenium compounds [6][7][8][9][10]. This potential in biological applications [11] of organoselenium compounds is enhanced by

• reactivity of organoselenium compounds, it is expected that chiral selenium containing derivatives could be synthetically useful as chiral auxiliaries or intermediates for the development of a novel asymmetric methodology platform [15][16][17][18]. Furthermore, compared with sulfur analogs [44], chiral