Diversity-oriented approach to 1,2-dihydroisoquinolin-3(4H)-imines via copper(I)-catalyzed reaction of (E)-2-ethynylphenylchalcone, sulfonyl azide and amine.

A three-component reaction of (E)-2-ethynylphenylchalcone, sulfonyl azide, and amine catalyzed by copper(I) chloride (5 mol%), in the presence of triethylamine, under mild conditions is described. This transformation proceeds efficiently to generate 1,2-dihydroisoquinolin-3(4H)-imines in good to excellent yields.

[1]  Jie Wu,et al.  A facile route to polysubstituted indoles via three-component reaction of 2-ethynylaniline, sulfonyl azide, and nitroolefin. , 2011, Organic letters.

[2]  E. Álvarez,et al.  Regioselective formation of 2,5-disubstituted oxazoles via copper(I)-catalyzed cycloaddition of acyl azides and 1-alkynes. , 2011, Journal of the American Chemical Society.

[3]  Katja Petzold,et al.  Novel tetrahydroisoquinoline based organocatalysts for asymmetric Diels-Alder reactions: insight into the catalytic mode using ROESY NMR and DFT studies , 2010 .

[4]  W. Yao,et al.  Three-component assembly and divergent ring-expansion cascades of functionalized 2-iminooxetanes. , 2010, Angewandte Chemie.

[5]  Sylvain Aubry,et al.  Synthesis of (±)-phthalascidin 650 analogue: new synthetic route to (±)-phthalascidin 622 , 2010 .

[6]  P. Andersson,et al.  Iridium-catalyzed asymmetric hydrogenation of olefins using TIQ phosphine–oxazoline ligands , 2010 .

[7]  D. Enders,et al.  Organocatalytic asymmetric synthesis of trans-1,3-disubstituted tetrahydroisoquinolines via a reductive amination/aza-Michael sequence. , 2010, Chemistry.

[8]  C. Bolm,et al.  Copper-catalyzed one-pot synthesis of alpha-functionalized imidates. , 2010, Chemical communications.

[9]  P. Lograsso,et al.  Tetrahydroisoquinoline derivatives as highly selective and potent Rho kinase inhibitors. , 2010, Journal of medicinal chemistry.

[10]  Lifen Wang,et al.  Copper-catalyzed multicomponent reaction: synthesis of 4-arylsulfonylimino-4,5-dihydrofuran derivatives. , 2010, The Journal of organic chemistry.

[11]  H. Langhals,et al.  Axially Extended Perylene Dyes , 2010 .

[12]  Jing Wang,et al.  Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins , 2010 .

[13]  P. Andersson,et al.  Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation , 2010 .

[14]  Wei Lu,et al.  A facile route to gamma-nitro imidates via four-component reaction of alkynes with sulfonyl azides, alcohols, and nitroolefins. , 2010, The Journal of organic chemistry.

[15]  Yanguang Wang,et al.  Copper‐Catalyzed One‐Pot Synthesis of Substituted Benzimidazoles , 2010 .

[16]  P. Andersson,et al.  Synthesis and Screening of C1‐Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions , 2010 .

[17]  U. Das,et al.  Towards chiral diamines as chiral catalytic precursors for the borane-mediated enantioselective reduction of prochiral ketones , 2009 .

[18]  P. Pihko,et al.  A highly enantioselective access to tetrahydroisoquinoline and beta-carboline alkaloids with simple noyori-type catalysts in aqueous media. , 2009, Chemistry.

[19]  E. Chang Copper-Catalyzed Multicomponent Reactions: Securing a Catalytic Route to Ketenimine Intermediates and their Reactivities , 2009 .

[20]  Min Zhang,et al.  Copper-Catalyzed Efficient Multicomponent Reaction: Synthesis of Benzoxazoline-Amidine Derivatives , 2009 .

[21]  S. Andujar,et al.  Structure-activity relationship of dopaminergic halogenated 1-benzyl-tetrahydroisoquinoline derivatives. , 2009, European journal of medicinal chemistry.

[22]  Wangze Song,et al.  Copper‐Catalyzed One‐Pot Synthesis of 2‐Alkylidene‐1,2,3,4‐ tetrahydropyrimidines , 2009 .

[23]  A. Forni,et al.  Selective Synthesis of Isoquinolin‐3‐one Derivatives Combining Pd‐Catalysed Aromatic Alkylation/Vinylation with Addition Reactions: The Beneficial Effect of Water , 2009 .

[24]  A. Hauser,et al.  A compactly fused pi-conjugated tetrathiafulvalene-perylenediimide donor-acceptor dyad. , 2009, Organic letters.

[25]  Sukbok Chang,et al.  A new entry of copper-catalyzed four-component reaction: facile access to alpha-aryl beta-hydroxy imidates. , 2009, Organic letters.

[26]  Yufang Xu,et al.  Selective and sensitive chromo- and fluorogenic dual detection of anionic surfactants in water based on a pair of "on-off-on" fluorescent sensors. , 2009, Chemistry.

[27]  U. Rinner,et al.  Recent progress in the total synthesis of naphthyridinomycin and lemonomycin tetrahydroisoquinoline antitumor antibiotics (TAAs). , 2008, Chemical Society reviews.

[28]  Sukbok Chang,et al.  Synthetic utility of ammonium salts in a Cu-catalyzed three-component reaction as a facile coupling partner. , 2008, The Journal of organic chemistry.

[29]  J. Stambuli,et al.  Calcium-catalyzed Pictet-Spengler reactions. , 2008, Organic letters.

[30]  Yuyang Jiang,et al.  Copper-Catalyzed Cycloaddition of Sulfonyl Azides with Alkynes to Synthesize N-Sulfonyltriazoles ‘on Water’ at Room Temperature , 2008 .

[31]  K. Sharpless,et al.  Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: dichotomy via a common pathway. , 2008, The Journal of organic chemistry.

[32]  Ji-Jun Chen,et al.  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro. , 2008, Bioorganic & medicinal chemistry letters.

[33]  Sukbok Chang,et al.  Room temperature copper-catalyzed 2-functionalization of pyrrole rings by a three-component coupling reaction. , 2008, Angewandte Chemie.

[34]  Sukbok Chang,et al.  Highly efficient synthesis of α-amino amidines from ynamides by the Cu-catalyzed three-component coupling reactions , 2008 .

[35]  Sukbok Chang,et al.  A new route to indolines by the Cu-catalyzed cyclization reaction of 2-ethynylanilines with sulfonyl azides. , 2008, Organic letters.

[36]  J. Wang,et al.  Copper-catalyzed multicomponent reaction: facile access to novel phosphorus amidines. , 2008, Organic letters.

[37]  Jing Wang,et al.  Efficient synthesis of 2-imino-1,2-dihydroquinolines and 2-imino-thiochromenes via copper-catalyzed domino reaction , 2008 .

[38]  Jing Wang,et al.  Facile access to pyrazolines via domino reaction of the Huisgen zwitterions with aziridines. , 2008, Organic letters.

[39]  Jing Wang,et al.  Copper-catalyzed multicomponent reaction: facile access to functionalized 5-arylidene-2-imino-3-pyrrolines. , 2007, Organic letters.

[40]  R. Ferraccioli,et al.  Stereoselective synthesis of 1,3-substituted tetrahydroisoquinolines through palladium-catalyzed three-component reaction , 2007 .

[41]  R. Grigg,et al.  Synthesis of carbo- and heterocycles via palladium catalysed cascade allene insertion–nucleophile incorporation–Michael addition processes , 2007 .

[42]  Dongping Cheng,et al.  Copper-catalyzed highly efficient multicomponent reactions: synthesis of 2-(sulfonylimino)-4-(alkylimino)azetidine derivatives. , 2007, Organic letters.

[43]  Sukbok Chang,et al.  Rate-accelerated nonconventional amide synthesis in water: a practical catalytic aldol-surrogate reaction. , 2007, Angewandte Chemie.

[44]  Yanguang Wang,et al.  Novel and efficient synthesis of iminocoumarins via copper-catalyzed multicomponent reaction. , 2006, Organic letters.

[45]  Minjae Lee,et al.  Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions. , 2006, Journal of the American Chemical Society.

[46]  N. Sotomayor,et al.  Conjugate additions of sulfur-stabilized anions to unsaturated lactams. Synthesis of polyfunctionalized benzo[a]quinolizinone systems. , 2006, The Journal of organic chemistry.

[47]  V. Fokin,et al.  Copper-catalyzed reaction cascade: direct conversion of alkynes into N-sulfonylazetidin-2-imines. , 2006, Angewandte Chemie.

[48]  Sukbok Chang,et al.  A facile access to N-sulfonylimidates and their synthetic utility for the transformation to amidines and amides. , 2006, Organic letters.

[49]  Sukbok Chang,et al.  Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water. , 2005, Journal of the American Chemical Society.

[50]  D. Enders,et al.  Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization. , 2005, The Journal of organic chemistry.

[51]  Sukbok Chang,et al.  Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine. , 2005, Journal of the American Chemical Society.

[52]  A. Głuszyńska,et al.  Enantioselective addition of methyllithium to a prochiral imine—the substrate in the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines , 2004 .

[53]  R. Ferraccioli,et al.  Synthesis of 1,2,3,4‐Tetrahydroisoquinolines and 2,3,4,5‐Tetrahydro‐1H‐2‐benzazepines Combining Sequential Palladium‐Catalyzed ortho Alkylation/Vinylation with Aza‐Michael Addition Reactions. , 2004 .

[54]  M. Chrzanowska,et al.  Asymmetric synthesis of isoquinoline alkaloids. , 2004, Chemical reviews.

[55]  R. Grigg,et al.  Synthesis of carbo- and heterocycles via a palladium-catalysed allene insertion–nucleophile incorporation–Michael addition cascade , 2003 .

[56]  A. Padwa,et al.  A short diastereoselective synthesis of the putative alkaloid jamtine, using a tandem pummerer/mannich cyclization sequence. , 2003, The Journal of organic chemistry.

[57]  Kung K Wang,et al.  Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides. , 2003, The Journal of organic chemistry.

[58]  M. Mori,et al.  Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: total synthesis of erythrocarine. , 2003, Organic letters.

[59]  V. Lynch,et al.  New strategy for the synthesis of tetrahydroisoquinoline alkaloids. , 2003, Organic letters.

[60]  Luke G Green,et al.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. , 2002, Angewandte Chemie.

[61]  T. Kan,et al.  Total synthesis of ecteinascidin 743. , 2002, Journal of the American Chemical Society.

[62]  Robin M. Williams,et al.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. , 2002, Chemical reviews.

[63]  A. Padwa,et al.  Total synthesis of (+/-)-jamtine using a thionium/N-acyliminium ion cascade. , 2002, Organic letters.

[64]  S. Danishefsky,et al.  Studies directed to the total synthesis of ET 743 and analogues thereof: an expeditious route to the ABFGH subunit. , 2002, Organic letters.

[65]  A. Głuszyńska,et al.  Enantioselective modification of the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline alkaloids synthesis of (−)-salsolidine and (−)-carnegine , 2000 .

[66]  J. Cook,et al.  The Pictet-Spengler condensation: a new direction for an old reaction , 1995 .

[67]  M. Rozwadowska Recent Progress in the Enatioselective Synthesis of Isoquinoline Alkaloids , 1994 .

[68]  S. Wallbaum,et al.  Enantioselective catalytic borane reductions of aromatic ketones: Syntheses and application of two chiral β-amino alcohols from (S)-porretine , 1992 .