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tert-Butyl Nitrite-Induced Cyclization Reactions in the Construction of Heterocyclic Compounds
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DOI：10.1002/asia.70624.png)
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Abstract
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Heterocyclic compounds are prominent in the field of organic chemistry. They have numerous applications, such as medicinal chemistry, natural products, biological activity, agrochemicals, dyes, and the pharmaceutical industry. The t-BuONO reagent has been utilized in synthetic organic chemistry to synthesize various heterocyclic compounds in recent years. Due to the properties of tert-Butyl nitrite as a mild, cost-effective, easy-to-handle, and environmentally friendly reagent, it is widely utilized. This reagent serves as a source of oxygen, nitrogen, nitric oxide, and nitrous oxide in organic reactions and is used as a co-catalyst or catalyst. tert-Butyl nitrite is employed in various reactions, including oxidation, radical initiation, and diazotization. These reactions facilitate cyclization processes like 5-exo-dig, 5-exo-trig, [3+2] cycloaddition, [3+2] dimerization, and 1,3-dipolar cycloaddition. This reactivity supports the construction of new types of heterocyclic compounds through simple synthetic procedures. In this review, we discuss the use of tert-Butyl nitrite in the synthesis of various heterocyclic compounds, providing detailed mechanisms and representative examples of substrate scope.
Keywords:
[3+2] cycloaddition reaction
1,3-dipolar cycloaddition
5-exo-trig cyclization
heterocyclic chemistry
tert-butyl nitrite
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