1719-18-2Relevant articles and documents
A metal-free tandem dehydrogenative α-arylation reaction of propargylic alcohols with 2-alkynylbenzaldoximes toward the synthesis of α-(4-bromo-isoquinolin-1-yl)-propenone skeletons
Abbasi Kejani, Alireza,Alatat, Khalil,Balalaie, Saeed,Bijanzadeh, Hamid Reza,Nikbakht, Ali
supporting information, p. 579 - 583 (2022/02/01)
A tandem reaction of 2-alkynylbenzaldoximes with propargylic alcohols has been developed for the synthesis of α-(4-bromo-isoquinolin-1-yl)-propenones. Employing 2-alkynylbenzaldoximes as a precursor in the presence of Br2 generates 4-bromo-isoquinoline-N-
Gold-catalyzed tandem annulations of pyridylhomopropargylic alcohols with propargyl alcohols
Li, Xue-Song,Xu, Dan-Tong,Niu, Zhi-Jie,Li, Ming,Shi, Wei-Yu,Wang, Cui-Tian,Wei, Wan-Xu,Liang, Yong-Min
supporting information, p. 832 - 836 (2021/02/16)
A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols is achieved, providing an atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer?Schuster rearrangement/Friedel?Crafts-type pathway. In this way, three C?C bonds and one C? O bond form to give a polycyclic skeleton in a one-pot process. Moreover, the products exhibit unique optical properties, which reveal their potential application value.
Calcium-Catalyzed Intramolecular Hydroamination-Deacylation Reaction of in situ formed β-Amino Allenes
Yaragorla, Srinivasarao,Latha, Dandugula Sneha,Rajesh, Pallava
supporting information, p. 5486 - 5492 (2021/12/10)
We have developed a simple, One-Pot, three-component reaction of tert-propargyl alcohols, primary amines and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives in good to excellent yields with large substrate diversity. An eco-friendly calcium catalyst catalyzes the reaction to form the key intermediate β-amino allene that undergoes subsequent Thorpe-Ingold effect assisted hydroamination and aromaticity driven deacylation reaction to yield fully substituted five and six-membered azacyclic compounds. (Figure presented.).
Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols
Kong, Xiangtao,Li, Xue-Song,Li, Yuke,Liang, Yong-Min,Liu, Hong-Chao,Niu, Zhi-Jie,Wang, Cui-Tian,Wei, Wan-Xu,Zhang, Zhe
supporting information, p. 9457 - 9462 (2021/12/14)
A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer–Schuster rearrangement, ring expansion, and Friedel–Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.
Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines
Du, Li-Juan,Han, Ya-Ping,Liang, Yong-Min,Zhang, Hong-Yu,Zhang, Yuecheng,Zhao, Jiquan
supporting information, (2020/03/04)
A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.
Synthesis of 2-(Isoquinolin-1-yl)prop-2-en-1-ones via Silver(I)-Catalyzed One-Pot Tandem Reaction of ortho-Alkynylbenzaldoximes with Propargylic Alcohols
Nikbakht, Ali,Balalaie, Saeed,Breit, Bernhard
supporting information, p. 7645 - 7648 (2019/10/14)
The silver(I)-catalyzed reaction of ortho-alkynylbenzaldoximes with propargylic alcohols represents a new strategy for the divergent one-pot synthesis of 2-(isoquinolin-1-yl) prop-2-en-1-ones via tandem 6-endo-cyclization, 1,3-dipolar cycloaddition, and intramolecular dehydrative opening of the 2,3-dihydroisoxazole ring. This synthetic protocol tolerates a wide variety of ortho-alkynylbenzaldoximes and propargylic alcohols and affords the corresponding products in excellent yields.
Br?nsted Acid-Mediated Formal [3+3] Annulation Between Propargylic Alcohols and 1,3-Diketones
Han, Ya-Ping,Li, Xue-Song,Zhu, Xin-Yu,Sun, Zhou,Li, Ming,Wang, Yu-Zhao,Liang, Yong-Min
supporting information, p. 870 - 874 (2017/12/26)
A Br?nsted acid-mediated formal [3+3] cascade annulation of propargylic alcohols with 1,3-diketones proceeds through a sequential Meyer?Schuster rearrangement/1,2-addition. This protocol, which has a wide scope and is conducted under an ambient atmosphere
Lewis Acid-Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4-Hydroxy-2H-chromen-2-ones
Han, Ya-Ping,Li, Xue-Song,Li, Ming,Zhu, Xin-Yu,Liang, Yong-Min
supporting information, p. 2796 - 2800 (2018/08/17)
A Lewis acid-catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2-c]chromen-5(2H)-one fragments has been developed using propargylic alcohols and 4-hydroxy-2H-chromen-2-on
Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (Z)-2-Styryl-1H-Indoles
Li, Xue-Song,Han, Ya-Ping,Zhu, Xin-Yu,Xia, Yu,Wei, Wan-Xu,Li, Ming,Liang, Yong-Min
supporting information, p. 4441 - 4445 (2018/10/15)
A novel copper(II) trifluoromethanesulfonate-catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)-2-styryl-1H-indoles as the initial substrates. This protocol, which entails a sequential Meyer-Schuster rearrangement/isomerization/-cyclization cascade, enables facile and atom-economical access to various pentacyclic compounds with broad functional-group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work. (Figure presented.).
Transition-Metal-Free, Br?nsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/-indolines: Highly Substituted δ- And α-Carbolines
Selvaraj, Karuppu,Swamy, K. C. Kumara
supporting information, p. 15043 - 15056 (2019/01/04)
Br?nsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction seque