2166-24-7Relevant academic research and scientific papers
Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation
Cao, Yuhui,Che, Jinteng,Chen, Han,Chen, Si-Cong,Fang, Xianhe,Guo, Yinliang,Guo, Zhixian,Kong, Lingran,Li, Chen,Lu, Jia-Tian,Luo, Tuoping,Zhang, Nan,Zhu, Qi
supporting information, p. 14046 - 14052 (2021/09/13)
A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.
One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives
Ananikov, Valentine P.,Ledovskaya, Maria S.,Polynski, Mikhail V.
, p. 2286 - 2297 (2021/07/20)
Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.
Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction
Akin, Esra Turan,Erdogan, Musa,Dastan, Arif,Saracoglu, Nurullah
, p. 5537 - 5546 (2017/08/22)
Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.
Unusual fragmentation of fulvene endoperoxides with phenyliodosyl bis(trifluoroacetate) (PIFA)
Oezer, Galip,Saracoglu, Nurullah,Balci, Metin
, p. 529 - 533 (2007/10/03)
Reaction of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate gave saturated fulvene endoperoxides containing the 1,2-dihydropyridazine ring. Treatment of dihydropyridazine endoperoxides with water followed by phenyliodosyl bis(trifluoroacetate) oxidation provided acrylic acid derivatives and dimethyl pyridazine-3,6-dicarboxylate.
Trapping of unsaturated fulvene endoperoxides with dimethyl 1,2,4,5- tetrazine-3,6-dicarboxylate: A new synthesis of alkylidene- and arylidenemalonaldehydes
?zer, Galip,Sara?o?lu, Nurullah,Balci, Metin
, p. 761 - 764 (2007/10/03)
Unsaturated fulvene endoperoxides (2a-e) were trapped with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (4). The formed saturated fulvene endoperoxides containig 1,2-dihydropyridazine ring (6a-e) were characterised by spectroscopic methods. Treatment of (6a-e) with cobalt(II) tetraphenylporphyrin (CoTPP) provided alkylidene-and arylidenemalonaldehydes (9a-e).
