One-Pot Synthesis of 3-Triazolyl-2-iminochromenes via a Catalytic Three Component Cascade Reaction

Qian, Wenyuan; Amegadzie, Albert; Winternheimer, David J.; Allen, Jennifer R.

doi:10.1021/ol401151z

Cited by 44 publications

(11 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition to the straightforward Cu-catalyzed azide–alkyne click chemistry, several multicomponent condensation-based click reactions are also known under one-pot mild conditions. − Surprisingly, out of these, very few are known in carbohydrate chemistry, probably due to the difficulty in handling the carbohydrate scaffold or the limited number of scientists working in related fields. Mukherjee et al utilized the one-pot multicomponent reaction for the development of biologically relevant furan-based glycoconjugates.…”

Section: Click-chemistry-inspired Synthesis Of Diverse Triazolyl Glyc...mentioning

confidence: 90%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

View full text Add to dashboard Cite

Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

show abstract

Section: Click-chemistry-inspired Synthesis Of Diverse Triazolyl Glyc...mentioning

confidence: 90%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The activating effect of the 1,2,3‐triazole moiety in the formation of 3‐triazolyl‐2‐iminochromenes 96 via a three‐component CuAAC‐condensation‐cyclization sequence was highlighted by Qian and co‐workers (Scheme ) 169. The triazole moiety enhances the CH‐acidity of the adjacent methylene group for the aldol condensation, as shown by control experiments where 2‐azidoacetonitrile could not undergo an aldol condensation under identical reaction conditions.…”

Section: Multiple Mcrs Coupled With Cuaacmentioning

confidence: 92%

“…[165] Just recently, upon employing dimedone and 1,3-cyclohexanedione as active methylene compounds, the cyclocondensation-CuAAC sequence gave rise to the formation [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo [2,1b]phthalazinetriones 94 in a one-pot fashion (Scheme 70). [169] The triazole moiety enhances the CH-acidity of the adjacent methylene group for the aldol condensation, as shown by control experiments where 2-azidoacetonitrile could not undergo an aldol condensation under identical reaction conditions. [168] The activating effect of the 1,2,3-triazole moiety in the formation of 3-triazolyl-2-iminochromenes 96 via a three-component CuAAC-condensation-cyclization sequence was highlighted by Qian and co-workers (Scheme 72).…”

Section: Multiple Mcrs Coupled With Cuaacmentioning

confidence: 92%

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

2015

View full text Add to dashboard Cite

The copper-catalyzed alkyne-azide cycloaddition (CuAAC) is a highly versatile, regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles under mild reaction conditions and has found numerous applications in medicinal, bioorganic, and materials chemistry in the past one and a half decades. By virtue of the enormous tolerance for functional groups and the mild reaction conditions, CuAAC has become increasingly important in combination with multicomponent reactions (MCR), either in a domino or in a consecutive fashion. While the majority of CuAAC-based MCR are founded on the in situ or en route generation of azides, one-pot generation of alkynes and the concatenation with other MCR are rapidly catching up and novel sequences for efficient one-pot syntheses of triazole-based structures in a multicomponent fashion are constantly evolving. This review summarizes important contributions of CuAAC-based MCR including MCRtype applications in polymer science.

show abstract

“…Then the neighboring methylene group would be activated and react with a salicylaldehyde inducing an aldol cyclization-dehydration sequence to give the corresponding 3-triazolyl-2-iminochromenes. The C(sp)-H, C(sp 2 )-H, and C(sp 3 )-H bonds were activated in one pot for this transformation [194] Murugavel and Punniyamurthy developed a CuI-catalyzed one-pot synthesis of iminocoumarin aryl methyl ethers from ynal, phenol, and sulfonyl azide via a cascade [3+2]-cycloaddition, 1,3-pseudopericyclic ketenimine rearrangement, 1,4-conjugate addition, and aldol-type condensation at room temperature under air [195] …”

Section: Copper-catalyzed Synthesis Of Coumarin Derivativesmentioning

confidence: 99%