Synthesis and reactivity of heterocyclic hydroxylamine-O-sulfonates

Abstract

The heterocyclic hydroxylamine-O-sulfonates constitute a novel family of formal O-substituted hydroxyguanidines and hydroxyamidines that serve as functional precursors to a variety of fused heterocyclic ring systems incorporating N-N, N-O, N-S, or N-N + moiety. They are readily accessible from the reaction of 2-chloroazoles, 2-chloroazines, and 2-chlorodiazines with hydroxylamine-O-sulfonic acid. They have a rich chemistry exemplified by tandem reactions, such as nucleophilic addition-electrophilic amination, nucleophilic addition-electrophilic 5-endo-trig cyclization or fluorogenic Mannich-electrophilic amination reaction. The heterocyclic hydroxylamine-O-sulfonates have significant potential for use in synthesis of anticancer, antiviral, and antimicrobial agents. The newly discovered fluorogenic reaction and fluorescent dyes (Safirinium-P and Safirinium-Q) have found applications in fluorescent detection and labeling.

New Pyrazolo-Benzimidazole Mannich Bases with Antimicrobial and Antibiofilm Activities

“…The substituted 1- H -aminobenzimidazoles 4a,b were obtained by the N -amination method with hydroxylamine-O-sulfonic acid (HOSA), under optimal reaction conditions of the substituted benzimidazoles 3a,b with yields of 62% and 63%, respectively ( Scheme 2 ). HOSA reacts in basic conditions as a nucleophile, while in neutral and acidic conditions it functions as an electrophile [ 52 , 53 ].…”

Experimental and theoretical studies on the tautomerism and reactivity of isoxazolo[3,4-b]quinolin-3(1H)-ones

“…20 The N-substituted derivatives of the bicyclic compound II obtained by Wierenga 21 exhibited a pronounced antileukemic 4 activity, and recently, we have described both the chemical and antimicrobial properties of 4,6-dimethylisoxazolo [3,4-b]pyridin-3(1H)-one III and its N-substituted derivatives. 2,22 In addition, based on compound III and isoxazolo [3,4- In this paper we wish to report the results of combined experimental and theoretical studies on the structure and specific reactivity of the ambident nucleophiles of type IV towards alkylating and acylating reagents. …”

Hydroxylamine-O-sulfonic acid as an efficient coreactant for luminol chemiluminescence for selective and sensitive detection

“…24 The heterocyclic hydroxylamine-O-sulfonates have significant potential for use in synthesis of anticancer, antiviral, and antimicrobial agents. 27 In this study, HOSA is exploited as an effective and stable coreactant for luminol CL. It can react with luminol to produce strong CL signals in the absence of any other activators.…”