The use of N-halosuccinimides for cyclization with the formation of five-membered heterocyclic compounds

Chiral non Aromatic Nitrogen-Heterocycles by Asymmetric Intramolecular Haloamination and Haloamidation

“…The outcome of halofunctionalization of unsaturated sulfamate ester derivatives 213 relied on both the halogen source and the catalyst employed. In fact, when the reaction was carried out with NBS in the presence of ligand 216 and Sc(OTf)3 a diastereomeric mixture of [1,2,3]oxathiazine 2,2dioxides syn-214 and anti-215 was obtained, the syn-bromoderivatives 83 being isolated as the major products in good yield and high enantioselectivity (Scheme 61). On the contrary, when the compounds 213 were treated with TsNCl2 as the donor of halenium ions, together with the ligand 219 and Lu(OTf)3, diastereomeric mixtures of anti-217 and syn-218 were isolated in good yield, and the major anti-isomers 217 were obtained with excellent enantioselectivity (Scheme 62) [153].…”

“…In the presence of a halenium ion source [1][2][3] an alkene can give rise to the corresponding intermediate haliranium ion 1 [4][5]. The subsequent nucleophilic attack by a nitrogen atom appropriately tethered on the carbon chain, occurring through an endo-or an exo-mode [6][7][8][9][10][11], leads to a variety of non-aromatic N-heterocycles, whose structure strongly depends on either the substrate geometry and the nucleophilic functionality involved [12][13][14][15][16][17] (Figure 1).…”

Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

“…Also, they provide many medicinal and biological applications such as antimicrobial, anticonvulsant, antibacterial, anticancer, anti-inflammatory and antifungal effects. [17,18] Pyrimidine and thiopyrimidine scaffolds have been attracted by many researchers because of chemotherapeutic and biological efficiency. Compounds containing pyrimidine ring system are pivotal derivatives that have a wide efficiency of pharmaceutical and medicinal activities such as antibacterial, anticancer, anxiolytic, antiviral, antioxidant, and antidepressant activities [19][20][21][22][23][24][25].…”

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

“…In the latter half of the 20th century, the halolactonizations of olefinic acids and amides, and the haloetherifications of olefinic alcohols were reported [ 4 , 5 , 6 , 7 ]. However, in the 21st century, there have been significant developments in halogen chemistry, as halogens have been determined to contribute to the control of high selectivities for the cyclization reactions [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. In modern halogen chemistry, halogen-controlled reaction strategies that can contribute toward selective transformations have, thus, become an important issue and are of utmost interest in organic synthesis.…”