Four-Membered Ring Systems

Anaya, Josefa; Sánchez, Ramón M.

doi:10.1016/b978-0-08-100755-6.00004-1

Cited by 4 publications

(2 citation statements)

References 520 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More broadly, this study contributes to the challenging research area devoted to the preparation of four-membered and other strained heterocycles. 26,27 ■ ASSOCIATED CONTENT * S Supporting Information…”

mentioning

confidence: 99%

Accessing the Rare Diazacyclobutene Motif

et al. 2018

View full text Add to dashboard Cite

A formal [2 + 2] cycloaddition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with electron-rich alkynyl sulfides and selenides is described. These investigations provide a convenient method to access diazacyclobutenes in good yield while tolerating a relatively broad substrate scope of thio-acetylenes. This method provides ready access to a unique and hitherto rarely accessible class of heterocycles. A combination of dynamic NMR, X-ray crystallography, and computation sheds light on the potential aromaticity of the scaffold.

show abstract

mentioning

confidence: 99%

Accessing the Rare Diazacyclobutene Motif

et al. 2018

View full text Add to dashboard Cite

show abstract

“…The value of such amines is considerable in synthesis, pharmacology, and medicine. [7][8][9][10] Herein, we present a method for the preparation of small (n = 3-5) and medium (n = 6-8) ring-sized azacycles that capitalizes on selective, intermolecular sp 3 -C-H amination of brominated hydrocarbon substrates (Scheme 1). The efficient functionalization of substrates in which the desired site of C-H oxidation is proximal to an electron-withdrawing halogen group underscores recent advances in Rh-catalyzed amination.…”

mentioning

confidence: 99%

Intermolecular sp3-C–H Amination for the Synthesis of Saturated Azacycles

Betz¹,

Chiappini

Bois³

2019

Preprint

View full text Add to dashboard Cite

The preparation of substituted azetidines and larger-ring, nitrogen-containing saturated heterocycles is enabled through efficient and selective intermolecular sp<sup>3</sup>-C–H amination of alkyl bromide derivatives. A range of substrates is demonstrated to undergo C–H amination and subsequent sulfamate alkylation in good to excellent yield. <i>N</i>-Phenoxysulfonyl-protected products can be unmasked under neutral or mild basic conditions to yield the corresponding cyclic 2° amines. The preparative convenience of this protocol is demonstrated through gram-scale and telescoped multi-step procedures. Application of this technology is highlighted in a nine step total synthesis of an unusual azetidine-containing natural product, penaresidin B.

show abstract

Heterocycles from Cycloaddition of Alkynes

2022

Addition Reactions With Unsaturated Hydrocarbons

View full text Add to dashboard Cite

Four-Membered Ring Systems

Cited by 4 publications

References 520 publications

Accessing the Rare Diazacyclobutene Motif

Accessing the Rare Diazacyclobutene Motif

Intermolecular sp3-C–H Amination for the Synthesis of Saturated Azacycles

Heterocycles from Cycloaddition of Alkynes

Contact Info

Product

Resources

About