17962-22-0Relevant articles and documents
Alkynylcyclohexanol chairs and twist-boats: Co2(Co)6 as a conformational switch
Deschamps,Kaldis,Lock,Britten,McGlinchey
, p. 8585 - 8591 (2001)
Treatment of 1-[axial]-(trimethylsilylethynyl)cyclohexan-1-ol with dicobalt octacarbonyl results in a conformational ring flip such that the bulky dicobalt-alkyne cluster moiety now occupies the favored equatorial site. However, when a 4-tert-butyl substi
Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds
Lv, Jiahang,Zhao, Binlin,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 691 - 694 (2020/07/13)
Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e
Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution
Chenna Reddy,Patil, Vineetkumar B.,Nawaz Khan, Fazlur Rahman,Saravanan, Vadivelu
, p. 1486 - 1497 (2019/04/04)
A new method has been developed for the synthesis of imidazo[1,2-a]pyridines, imidazo[2,1-b]thiazoles, and benzo[d]imidazo[2,1-b]thiazoles attached to a cycloalkyl or saturated heterocycle containing a tertiary hydroxy substitution. Readily available substituted 2-aminopyridines, 2-aminothiazoles, and 2-aminobenzothiazoles were treated with bromohydroxycycloalkyl ethanones to afford the desired products in good yields.
Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
Pradhan, Tapas R.,Mohapatra, Debendra K.
supporting information, p. 3605 - 3611 (2019/07/04)
A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).
Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation
Roy, Satyajit,Khatua, Hillol,Das, Sandip Kumar,Chattopadhyay, Buddhadeb
supporting information, p. 11439 - 11443 (2019/07/17)
A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.
Boron Trichloride-Mediated Synthesis of Indoles via the Aminoboration of Alkynes
Lv, Jiahang,Zhao, Binlin,Liu, Li,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
supporting information, p. 4054 - 4059 (2018/09/25)
We describe an efficient catalyst- and metal-free aminoboration of alkynes to 3-borylated indoles using one of the least expensive boron sources, BCl3. The major dichloro(indolyl)borane products can be used for the in situ construction of usefu
Gold-Catalyzed Intermolecular Ynamide Amination-Initiated Aza-Nazarov Cyclization: Access to Functionalized 2-Aminopyrroles
Shu, Chao,Wang, Yong-Heng,Shen, Cang-Hai,Ruan, Peng-Peng,Lu, Xin,Ye, Long-Wu
supporting information, p. 3254 - 3257 (2016/07/13)
A novel gold-catalyzed intermolecular ynamide amination-initiated aza-Nazarov cyclization has been developed, allowing the facile and efficient synthesis of various 2-aminopyrroles in moderate to good yields. Furthermore, a mechanistic rationale for this
Palladium-catalyzed difunctionalization of internal alkynes via highly regioselective 6- endo cyclization and alkenylation of enynoates: Synthesis of multisubstituted pyrones
Tian, Pan-Pan,Cai, Sai-Hu,Liang, Qiu-Ju,Zhou, Xing-Yi,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 1636 - 1639 (2015/04/14)
An efficient Pd(II)-catalyzed difunctionalization reaction of internal alkynes is reported. In this reaction, various enynoates and electron-deficient alkenes were used for the syntheses of useful highly substituted pyrone derivatives via a 6-endo cycliza
Efficient synthesis and antibacterial activities of some novel 1,2,3-triazoles prepared from propargylic alcohols and benzyl azides
Hosseinzadeh, Rahman,Abolfazli, Mohammadreza Khadem,Mohseni, Mojtaba,Mohadjerani, Maryam,Lasemi, Zahra
, p. 1298 - 1305 (2015/04/27)
A simple and effective procedure for regioselective preparation of 1,2,3-triazoles from benzyl azides and propargylic alcohols is described using CuSO4·5H2O and sodium ascorbate. To screen the antibacterial activity of some newly synthesized triazole derivatives, minimum inhibitory concentration of 3d and 3k was evaluated against gram positive Staphylococcus aureus and Bacillus subtilis and gram negative Escherichia coli and Pseudomonas aeruginosa.
Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study
Tejedor, David,Cotos, Leandro,Márquez-Arce, Daniel,Odriozola-Gimeno, Mikel,Torrent-Sucarrat, Miquel,Cossío, Fernando P.,García-Tellado, Fernando
supporting information, p. 18280 - 18289 (2015/12/24)
The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.
