408526-05-6Relevant academic research and scientific papers
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-
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.
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
TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
, p. 7616 - 7625 (2014/09/16)
A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
Efficient synthesis of di- and trisubstituted 2-aryloxazoles via ytterbium(III) triflate catalyzed cyclization of tertiary propargylic alcohols with aryl amides
Zhang, Xiaoxiang,Teo, Wan Teng,Chan, Philip Wai Hong
supporting information; experimental part, p. 331 - 337 (2011/02/17)
An efficient synthetic method to prepare di- and trisubstituted 2-aryloxazoles based on Yb(OTf)3 catalyzed cyclization of trisubstituted propargylic alcohols with aryl amides is described. The reaction was accomplished in moderate to excellent product yields and with complete regioselective control. The mechanism is suggested to involve activation of the starting alcohol by the metal catalyst that results in its ionization. Subsequent cyclization of this newly generated carbocationic species with the aryl amide then affords the oxazole. In view of the mild conditions along with the low cost, commercially availability of Yb(OTf)3 and its high tolerance to air and moisture, the present synthetic approach offers an operationally simplistic and convenient route to this important aromatic heterocycle.
Bronsted acid catalyzed cyclization of propargylic alcohols with thioamides. Facile synthesis of Di- and trisubstituted thiazoles
Zhang, Xiaoxiang,Teo, Wan Teng,Sally,Chan, Philip Wai Hong
supporting information; experimental part, p. 6290 - 6293 (2010/11/18)
Figure presented. A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH·H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.
Ytterbium(III) triflate catalyzed tandem friedel-crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols
Zhang, Xiaoxiang,Teo, Wan Teng,Chan, Philip Wai Hong
supporting information; experimental part, p. 4990 - 4993 (2009/12/28)
A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel - Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished In moderate to excellent yields and regioselectivity under mild conditions and offers a straightforward and convenient one step synthetic route to bioactive indenols and its derivatives.
