Synthesis of N‐heterocycles via [4 + 3] cycloaddition of azomethine imine

Madan Sau; Kshitiz Verma; Tapas Das

doi:10.1002/jhet.4095

Microwave-assisted facile synthesis of [a]-annelated pyrazolopyrroloindoles via intramolecular azomethine imine 1,3-dipolar cycloaddition

Tetrahedron Letters ◽

10.1016/j.tetlet.2014.03.134 ◽

2014 ◽

Vol 55 (19) ◽

pp. 3064-3069 ◽

Cited By ~ 25

Author(s):

Anand H. Shinde ◽

Shinde Vidyacharan ◽

Duddu S. Sharada

Keyword(s):

Dipolar Cycloaddition ◽

Facile Synthesis ◽

Azomethine Imine ◽

Microwave Assisted

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Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks via Intramolecular Azomethine Imine 1,3-Dipolar Cycloaddition (IAIDC)

ChemistrySelect ◽

10.1002/slct.201801269 ◽

2018 ◽

Vol 3 (24) ◽

pp. 6960-6964 ◽

Cited By ~ 9

Author(s):

Manickam Bakthadoss ◽

Vishal Agarwal

Keyword(s):

Dipolar Cycloaddition ◽

Azomethine Imine

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Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Synthesis ◽

10.1055/s-0037-1610284 ◽

2018 ◽

Vol 50 (23) ◽

pp. 4501-4524 ◽

Cited By ~ 4

Author(s):

Jurij Svete ◽

Uroš Grošelj ◽

Franc Požgan ◽

Bogdan Štefane

Keyword(s):

Experimental Data ◽

Click Chemistry ◽

Organic Synthesis ◽

Present Review ◽

Metal Free ◽

Azomethine Imine ◽

Cuaac Reaction ◽

Azomethine Imines

Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

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