Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3+2] Cycloaddition:  Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif

Kumaraswamy, Gullapalli; Ankamma, Kukkadapu; Pitchaiah, Arigala

doi:10.1021/jo701724f

Cited by 91 publications

(38 citation statements)

References 19 publications

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“…They utilized the click‐chemistry to synthesize small pharmacophore containing molecules, N ‐tosylamino 1, 2, 3‐triazoles 43 , from N ‐tosylaziridines 42 with sodium azide using ecofriendly PEG‐400. This reaction proceeded through formation of an azidoamine intermediate followed by an in situ click‐cyclization by 5 mol% of Copper (I) iodide as a catalyst and an alkyne . (Scheme ).…”

Section: Polyethylene Glycol (Peg) Mediated Aziridine Ring Openingmentioning

confidence: 99%

Aziridine Ring Opening: An Overview of Sustainable Methods

et al. 2018

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Aziridines are important synthetic intermediates as many diverse class of compounds could be produced by opening their strained ring. Hence, many publications could be found in the literature describing various approaches for the ring‐opening reactions of aziridines. Recently, simple, cost‐effective and greener approaches for these reactions have attracted significant attention of researchers. In this review, we have presented several sustainable methods for ring opening of various substituted aziridines.

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Section: Polyethylene Glycol (Peg) Mediated Aziridine Ring Openingmentioning

confidence: 99%

Aziridine Ring Opening: An Overview of Sustainable Methods

et al. 2018

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“…[88] This approach with a concomitant three-component one-pot synthesis allowed the application of a wide variety of substrates generating high yields with excellent ee values of the products. Inspired by this approach, a novel and efficient one-pot synthesis of 1,2,3-triazolo b-hydroxy (40) or b-tosylamino (41) derivatives has been derived by ring opening of epoxides and aziridines by azides and their subsequent click reaction using PEG as an environmentally benign reaction medium (Scheme 27).…”

Section: Azide Formation From Epoxide Openingmentioning

confidence: 99%

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

2015

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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.

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“…Nandi and co‐workers also showed the Copper catalyzed ‘click’ reaction . Besides, the synthesis of β‐hydroxy‐1,2,3‐triazoles has also been performed through ‘click’ reaction by the use of suitable epoxides with CuSO 4 or CuI . Francisco Alonso and Patrick Pale, have explored Cu(I)‐zeolite based catalytic method to have β‐hydroxy‐1,2,3‐triazoles.…”

Section: Introductionmentioning

confidence: 99%

“…[36] Besides, the synthesis of β-hydroxy-1,2,3-triazoles has also been performed through 'click' reaction by the use of suitable epoxides with CuSO 4 [37] or CuI. [38] Francisco Alonso and Patrick Pale, [39,40] have explored Cu(I)-zeolite based catalytic method to have βhydroxy-1,2,3-triazoles. Kumar et al developed the synthesis of β-hydroxy-1,2,3-triazoles by using CuFe 2 O 4 magnetic nano particles.…”

Section: Introductionmentioning

confidence: 99%

A Cu(II)‐Inorganic Co−Crystal as a Versatile Catalyst Towards ‘Click’ Chemistry for Synthesis of 1,2,3‐triazoles and β‐hydroxy‐1,2,3‐triazoles

et al. 2020

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A novel Cu(II) inorganic co‐crystal (CuICC) i. e. {[Cu(IMA)(2,2′‐bipyridine)(H2O)]2 ⋅ [Cu2(IMA)2(2,2′‐bipyridine)2] ⋅ 6H2O} [where IMA=isopropylmalonic acid] has been synthesized. The inorganic co‐crystal of Cu(II) has been exploited as the versatile efficient catalyst for the cost effective facile synthetic approaches towards ‘click’ reaction which is effective for the several marked organic syntheses of 1,2,3‐triazoles and β‐hydroxy‐1,2,3‐triazoles. The catalytic process was performed through the single pot reaction based aerial synthetic protocol that does not need to perform any chromatographic purification technique. Interestingly, the CuICC acts as heterogeneous catalyst for the synthesis of 1,2,3‐triazoles, whereas its homogeneous catalytic role has been found for the synthesis of β‐hydroxy‐1,2,3‐triazoles.

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Tandem Epoxide or Aziridine Ring Opening by Azide/Copper Catalyzed [3+2] Cycloaddition: Efficient Synthesis of 1,2,3-Triazolo β-Hydroxy or β-Tosylamino Functionality Motif

Cited by 91 publications

References 19 publications

Aziridine Ring Opening: An Overview of Sustainable Methods

Aziridine Ring Opening: An Overview of Sustainable Methods

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

A Cu(II)‐Inorganic Co−Crystal as a Versatile Catalyst Towards ‘Click’ Chemistry for Synthesis of 1,2,3‐triazoles and β‐hydroxy‐1,2,3‐triazoles

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