[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Zhang, Xueming; Xu, Xianxiu; Zhang, Dawei

doi:10.3390/molecules22071131

Cited by 8 publications

(5 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As shown in Scheme 3 , the electron-withdrawing groups may be esters, amides, ketones, nitros, cyanos, aryls, etc. [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ]. Based on the different types of electron-withdrawing group attached to the alkenes, they are classified and described in order ( Scheme 3 ).…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

“…In 2017, our research group discovered that TosMIC 16 can undergo a [3+2] cycloaddition reaction with a styrylisoxazole compounds 130 to construct a series of 3-isoxazole disubstituted pyrrole derivatives 131 ( Scheme 40 ) [ 60 ]. Under the same optimized reaction condition, the synthesis of the 3-isoxazole trisubstituted pyrrole derivatives 132 was achieved by using the TosMIC derivatives 16 ( Scheme 41 ) [ 60 ]. This transformation is operationally simple, high-yielding, and displays broad substrate scope.…”

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

Self Cite

View full text Add to dashboard Cite

Pyrrole and its polysubstituted derivatives are important five-membered heterocyclic compounds, which exist alone or as a core framework in many pharmaceutical and natural product structures, some of which have good biological activities. The Van Leusen [3+2] cycloaddition reaction based on tosylmethyl isocyanides (TosMICs) and electron-deficient compounds as a substrate, which has been continuously developed due to its advantages such as operationally simple, easily available starting materials, and broadly range of substrates, is one of the most convenient methods to synthetize pyrrole heterocycles. In this review, we discuss the different types of two carbon synthons in the Van Leusen pyrrole reaction and give a summary of the progress of these synthesis methods in the past two decades.

show abstract

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Section: Synthesis Of Pyrrole Derivatives By [3+2] Cycloaddition Omentioning

confidence: 99%

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Zhang

2018

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

“…They distinctly enhance certain features, such as benzobicylon, thiamphemcol, and HDACI . It can also serve as a protecting group for functional groups or a “baton” that adds to and then leaves from an intermediate in organic synthetic reactions. , These benefits contribute to the diversity of their synthetic methods. With this strategy, the reaction of 1g with chlorobenzene could be easily performed at ambient temperature affording 3y in 81% yield after 3 h. This valuable molecule ( 3y ) now is a commercial reagent and could be used for the synthesis of poly(oxy-1,4-phenylenesulfonyl-1,4-phenylene), Acedapsone, Dapsone, and other useful valuable derivatives via a simple derivatization reaction (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Regiospecific Cleavage of S–N Bonds in Sulfonyl Azides: Sulfonyl Donors

et al. 2019

View full text Add to dashboard Cite

Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.

show abstract

“…All the compounds are well characterized using spectral analysis. [49] Product formation was explained by classical van Leusen mechanism as exemplified in Scheme 67.…”

Section: Synthesis Of Tethered/linked Heterocyclesmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

View full text Add to dashboard Cite

p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

show abstract

[3+2] Cycloaddition of Tosylmethyl Isocyanide with Styrylisoxazoles: Facile Access to Polysubstituted 3-(Isoxazol-5-yl)pyrroles

Cited by 8 publications

References 56 publications

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds

Regiospecific Cleavage of S–N Bonds in Sulfonyl Azides: Sulfonyl Donors

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Contact Info

Product

Resources

About