850570-01-3Relevant academic research and scientific papers
Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines
Cao, Shanshan,Li, Linxuan,Liu, Zhaohong,Ning, Yongquan,Wu, Yong,Zanoni, Giuseppe,Zhang, Qi,Zhang, Xinyu
supporting information, p. 3674 - 3679 (2021/05/31)
An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C= C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.
Facile access to highly functionalized hydroisoquinoline derivatives: Via phosphine-catalyzed sequential [3+3]/[3+3] annulation
Li, Ning,Jia, Penghao,Huang, You
supporting information, p. 10976 - 10979 (2019/09/16)
An unprecedented sequential [3+3]/[3+3] annulation of allenoates and dienes catalyzed by phosphine has been developed, which provides novel and facile access to highly functionalized hydroisoquinoline derivatives. The reaction features a wide reaction scope and mild reaction conditions. δ-sulfonamido-allenoates, acting as a five-atom unit, represent a new synthon in the reactions of allenoates.
Reaction Route and Mechanism of the Direct N-Alkylation of Sulfonamides on Acidic Mesoporous Zeolite β-Catalyst
Fu, Wenqian,Shen, Runsheng,Bai, Enhui,Zhang, Lei,Chen, Qun,Fang, Zhongxue,Li, Guangchao,Yi, Xianfeng,Zheng, Anmin,Tang, Tiandi
, p. 9043 - 9055 (2018/09/11)
Development of highly active heterogeneous catalysts with strong acidity and mesoporous structure is a highly attractive strategy for organic synthesis. In this study, a mesoporous zeolite beta (HBeta-M) with bulky particle size and strong acidity was synthesized and used in the direct N-alkylation of sulfonamides with alcohols. The strongly acidic HBeta-M had a higher intrinsic activity with initial turnover frequency of 11 × 10-2 s-1 than those of H-form mordenite nanosheets (3.3 × 10-2 s-1) and montmorillonite (4.0 × 10-2 s-1) catalysts. The experiment and characterization results demonstrate that there are two parallel reaction routes on the acidic catalysts. One route is the reaction of benzhydrol with p-toluenesulfonamide (route I). Another route is the reaction of dibenzhydryl ether, arising from route I, with p-toluenesulfonamide (route II), which is found in this work. The reaction rate of route I (13 × 10-3 mol kg-1 s-1) was higher than that of route II (9.8 × 10-3 mol kg-1 s-1) on HBeta-M, but route II predominantly contributed to the formation of the target product with high selectivity. Hereby, a complete reaction mechanism is proposed in this work.
O-Transfer-facilitated cyclizations of propargylamides with TMSN3: Selective synthesis of tetrazoles and dihydroimidazoles
Hu, Yancheng,Yi, Ruxia,Yu, Xinzhang,Xin, Xiaoyi,Wang, Chunxiang,Wan, Boshun
supporting information, p. 15398 - 15401 (2015/10/20)
An unprecedented formal [3+2] annulation of propargylamides with TMSN3 to deliver functionalized tetrazoles is developed. Oxygen-atom transfer (OAT) from the amide group to the CC bond was realized via a NIS-triggered-cyclization/ring-opening cascade pathway. The OAT process enables the amide to serve as a two-atom unit in the reactions. Notably, in situ umpolung of azide occurred when terminal propargylamides were employed in this reaction, providing an array of diiodomethylated dihydroimidazoles.
Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction
Chachignon, Helene,Scalacci, Nicoloì,Petricci, Elena,Castagnolo, Daniele
, p. 5287 - 5295 (2015/05/27)
Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.
Cyclobutene formation in PtCl2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes
Ni, Zhenjie,Giordano, Laurent,Tenaglia, Alphonse
, p. 11703 - 11706 (2014/10/15)
Aza(oxa)bicyclo[3.2.0]heptenes are accessed through the PtCl 2-catalyzed cycloisomerizations of heteroatom-tethered 1,6-enynes featuring a terminal alkyne and amide as the solvent. It is shown that the weak coordinating properties of the solven
SnCl2-catalyzed propargylic substitution of propargylic alcohols with carbon and nitrogen nucleophiles
Masuyama, Yoshiro,Hayashi, Miki,Suzuki, Noriyuki
, p. 2914 - 2921 (2013/07/05)
A weak Lewis acid, tin(II) chloride, which is insensitive to water and air, functioned as a catalyst for the propargylic substitution of secondary propargylic alcohols with carbon nucleophiles, such as electron-rich arenes, heteroarenes, and 1,3-dicarbony
Facile synthesis of dihaloheterocycles via electrophilic iodocyclization
Yang, Fan,Jin, Tienan,Bao, Ming,Yamamoto, Yoshinori
supporting information; scheme or table, p. 10147 - 10155 (2012/01/03)
An efficient and facile electrophilic iodocyclization for the synthesis of various O-, N-, and S-containing dihaloheterocycles has been developed. A wide range of the substituted propargyl alcohols having -OH, -NTs, and -SAc functional groups reacted with molecular iodine or bromoiodine at ambient temperature to produce the corresponding dihalogenated O-, N-, and S-containing five- and six-membered heterocycles in good to high yields; Under optimized solvent conditions, the reactions of various substituted but-2-yn-1-ones bearing -OH, -NTs, and -SAc functional groups at C4-position, with iodine or bromoiodine at ambient temperature afforded the corresponding 3,4-diiodo- and 3-bromo-4-iodo-substituted furans, pyrroles, and thiophenes in good to high yields. Further transformation of the resulting iodine- or bromine-containing products to polyaromatics potentially of useful as organo-material intermediates has been investigated.
Catalytic dicyanative 5-exo- And 6-endo-cyclization triggered by cyanopalladation of alkynes
Arai, Shigeru,Koike, Yuka,Nishida, Atsushi
supporting information; experimental part, p. 893 - 900 (2010/07/06)
A stereoselective dicyanative 5-exo- and 6endo-cyclization using various enynes has been investigated. The mode of cyclization is critically controlled by the structure of the substrates. For example, N-allyl derivatives prefer 5-exo-cyclization, while methacryloyl amides are transformed to the corresponding lactams with tetra substituted carbons at the alpha-position via 6-endo-cyclization. Both reactions include syn-cyanopalladation to carbon≡carbon triple bonds in the initial step, and sequential cyclization followed by reductive elimination in one operation enables the construction of the highly functionalized nitrogen heterocycles. The scope of suitable substrates and a proposed mechanism are also described.
Redox-neutral synthesis of β-amino aldehydes from imines by an alkynylation/hydration sequence
Labonne, Aurelie,Zani, Lorenzo,Hintermann, Lukas,Bolm, Carsten
, p. 5704 - 5708 (2008/02/09)
(Chemical Equation Presented) N-Protected β-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of
