Ultrasonic irradiation of the ullmann condensation: Application to the preparation of dioxolo, dioxino, cyclopent, and imidazolo anthranilic acid derivatives

Abstract

The synthesis of N-aryl anthranilic acid derivatives bearing dioxolo, dioxino, cyclopent, and imidazolo supplementary ring systems is reported. The Ullmann-Goldberg condensation of the N-aryl anthranilic acid is improved in yield and reaction time, compared to conventional heating; by ultrasonic irradiation. [5]. In that case, we developed a method using ultrasonic irradiation (UI) to increase the Ullmann condensation in the synthesis of anthranilic acids used as intermediates, according to the acridine synthetic pathway shown in Scheme 1. Scheme 1To improve this method, we chose different acridine analogues already described with poor yields, and compared the classical Ullman-Jourdan condensation [6] with ultrasound.

1H and 13C chemical shifts for acridines: Part XVII. (1,3‐Benzothiazol‐2‐yl)amino‐9(10H)‐acridinone derivatives

“…6 As part of our program on modified acridines as topoisomerase-target drug, 7,8 we were interested in preparing new acridine compounds with a supplementary benzothiazole ring since the latter compound also showed interesting activity as an anti-cancer drug. In this paper we report the complete 1 H and 13 C NMR chemical shift assignments obtained from one-and twodimensional NMR techniques for acridin-9(10H)-ones substituted with (6-X-1,3-benzothiazol-2-yl)amino groups (X D H, NH 2 and NO 2 ).…”

A Facile and Rapid Method for Preparation of Thiazine and Thiadiazine Derivatives by Sonication Technique

“…[1][2][3][4][5] The use of ultrasound irradiation technique for activating various reactions is well documented in the literature, such as synthesis of azoles and diazenes, 6 Reformatsky reaction, 7 oxidation of substrates such as hydroquinones, 8 conversion of nitro compounds to carbamates, 9 pinacol coupling, 10 and Ullmann condensation. 11 Carbostyril 12 and dimedone 13 constitute a unique group of compounds due to the simultaneous presence of characteristic features such as a β-diketone group as a starting material. Thazines are known to exhibit various types of biological activities such as Ca 2+ antagonist; blood platelet aggregation inhibitors; 14 and antipsychotic, 15 antiviral, 16 antimicrobial, 17 and antihypertensive 18 agents.…”

Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part I

“…Robin and co-workers successfully synthesized acridine derivatives using this method (Robin, M., et al, 2002). In order to replace dry organic solution with more environmentally benign ones: Pellon et al extended the synthesis of halobenzoic acid and alkylamine in the presence of water as a solvent with copper under probe sonication (Pellon, R. F., et al, 2005 ).…”