Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems

Abstract

The review is devoted to modern trends in the chemistry of nitrogen-, oxygen-and sulfur-containing monocyclic, polynuclear and benzo(hetero)annulated heterocyclic compounds. Methods for the synthesis and chemical reactivity of furazan, furoxan, thiazole, thiadiazole, dithiazole, thiophene, glycoluril, imidazotriazine, diaziridine and other heterocycles are discussed. Characteristic features of reactions depending on the structure of the starting compounds, intermediates and reaction medium (organic solvents, ionic liquids) and mechanistic aspects of the most interesting transformations are considered. Data on the biological activities and prospects for practical applications of the indicated heterocyclic systems are presented. The bibliography includes 383 references.

Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors

“…Among the variety of nitrogen–oxygen organic and organometallic compounds capable of NO release under physiological conditions, the furoxan (1,2,5-oxadiazole 2-oxide) scaffold has attracted considerable attention [ 69 , 70 , 71 , 72 ] mainly due to the high stability of the furoxan cycle under ambient conditions and absence of nitrate tolerance under continuous therapy [ 23 ]. Long-term investigations of Prof. Alberto Gasco [ 73 , 74 ] revealed a possibility of regioisomeric furoxans with different positions of the N -oxide group to produce NO in significantly different amounts.…”

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

“…in 2008 and in 2011 [2a,b] . Despite few more articles [2c–e] were reported independently by Lumb and Makhova, discussing various features of diaziridines, including structural and biological applications, the comprehensive account on the synthesis and applications were not accounted post 2011. However, owing to the unique reactivities and properties, the attention upon these two moieties were expanded significantly in multiple directions, and are emerged as crucial building blocks in natural products, drug molecules and versatile enantiopure organic substrates in several enantioselective transformations.…”

New Trends in Diaziridine Formation and Transformation (a Review)

“…An important intermediate and precursor in organic chemistry, diaziridine [1] is a highly strained three-membered heterocycle with two nitrogen atoms [2]. The other excellent properties of diaziridine include a weak N-N bond, low toxicity, hydrazine aminal duality [3], and neurotropic activity [4]. Diaziridines, independently discovered by three research groups (Schmitz's, Paulsen's, and Abendroth and Henrich's research groups) between 1958 and 1959, progressively achieved popularity in the field of chemistry over the two decades following these first publications [5].…”

“…As for N,N-disubstituted diaziridine 3, these valuable heterocycles have also been used as a versatile reagent via selective C-N or N-N cleavage in organic synthesis, particularly their bicyclic analogues of 1,5-diazabicyclo[3.1.0]-hexanes, which possess a strained cis-N,Ndisubstituted diaziridine fragment for 1,3-dipolar cycloaddition [17]. The advancements in substituted diaziridine with respect to its nitrogen atom(s) synthesis and applications have been summarized in several reviews [3][4][5][18][19][20]. On the basis of these excellent reviews, only a few studies have been fully dedicated to investigating the potential properties diaziridine with respect to its monocyclic synthetic methods [20] or its reactivity of these excellent reviews, only a few studies have been fully dedicated to investigating the potential properties diaziridine with respect to its monocyclic synthetic methods [20] or its reactivity towards electrophilic reagents [5].…”