Unsaturated four-membered N-heterocycles: From synthesis to applications

Didier, Dorian; Baumann, Andreas N.; Eisold, Michael

doi:10.1016/j.tetlet.2018.09.055

Cited by 27 publications

(22 citation statements)

References 98 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Maruoka group overcame the requirement for cyclic imines by demonstrating that N-(arylsulfonyl)imines (37) undergo [2 + 2] photocycloadditions with styrenyl alkenes (38) such as styrene or benzofuran when irradiated with 365 nm UV light, providing protected azetidines (40-42) in 20-83% yield (Fig. 13).…”

Section: Scope and Limitationsmentioning

confidence: 99%

“…Specifically, the reaction between an imine and an alkyne provides 2-azetines as photocycloadducts. Although the products represent interesting scaffolds, 38 accessing these via aza Paternò–Büchi reactions has been met with limited success. Mei-Gong and coworkers reported that 6-azauracil 49 undergoes [2 + 2] photocycloaddition with alkynes such as propargyl alcohol ( 48 ) ( Fig.…”

Section: Scope and Limitationsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of azetidines by aza Paternò–Büchi reactions

2020

View full text Add to dashboard Cite

show abstract

Section: Scope and Limitationsmentioning

confidence: 99%

Section: Scope and Limitationsmentioning

confidence: 99%

Synthesis of azetidines by aza Paternò–Büchi reactions

2020

View full text Add to dashboard Cite

show abstract

“…[6][7][8][9] These small and strained N-heterocycles are potentially promising for applications in drug design and biomedical research. 7,10 However the synthesis of benzazetidine and their reactivity remain largely unexplored because of the scarcity of effective synthetic methodologies towards this class of compounds [6][7][8][9][11][12][13] which stems from their relative instability. 6,8,14 They also attract interest because, in the family of the fused four-membered N-heterocycles, the fused β-lactams account for the largest share of research efforts and, consequently, there is a lack of diversity among these compounds in the literature.…”

mentioning

confidence: 99%

Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups

et al. 2019

View full text Add to dashboard Cite

Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, 4-membered hemiaminal structure. This method affords several benzazetidine in moderate to good yields (up to 81%), it uses inexpensive materials and does not require catalysts based on transition metals. The high ring strain energy of these benzazetidine systems was estimated by DFT calculations to be about 32 kcal mol-1. This synthesis can be applied also on gram scale with reaction yield essentially unchanged.

show abstract

“…One of the challenges impeding the development of this field is the lack of general methods for preparing unsaturated 4‐membered ring N ‐heterocycles. Here we highlight several creative recent approaches to the preparation of azetes, dihydroazetes, and azetidine nitrones that have addressed this limitation, as well initial studies that emphasize the importance of continuing to explore the reactivity of these compounds for diversity‐oriented synthesis of azetidines . The intention of this section of the review is to showcase this burgeoning field and garner excitement towards pursuing methods to prepare and functionalize unsaturated azetidine derivatives as a facile alternative entry to desirable functionalized azetidines.…”

Section: Development Of Unsaturated Azetidines As Precursors For Divementioning

confidence: 99%

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

Reidl

Anderson

2019

Asian J Org Chem

View full text Add to dashboard Cite

Azetidines are unusual heterocyclic motifs that comprise key components of biologically active molecules and provide desirable structural properties for drug discovery. While a variety of methods have been designed for the synthesis of azetidines, screening and optimization studies often require systematic and versatile strategies for varying structural characteristics. With this need in mind, this review surveys methods for the divergent preparation of substituted azetidines from starting materials that contain a 4-membered azacycle. The scope and tolerance of azetidine functionalization reactions are described including approaches such as lithiation and electrophilic trapping, nucleophilic displacement, and transition metal catalysis. To complement this discussion, opportunities for using unsaturated azetidines as precursors to functionalized saturated analogues are also examined as an emerging alternative tactic towards the diversity-oriented preparation of these strained heterocycles. The aim of this Minireview is to identify recent advances, as well as areas where further development is needed, to continue to inspire innovative solutions to the divergent synthesis of functionalized azetidines.[a] T.

show abstract

Unsaturated four-membered N-heterocycles: From synthesis to applications

Cited by 27 publications

References 98 publications

Synthesis of azetidines by aza Paternò–Büchi reactions

Synthesis of azetidines by aza Paternò–Büchi reactions

Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

Contact Info

Product

Resources

About