A new protocol for the synthesis of primary, secondary and tertiary anthranilamides utilizing N-(2-aminoarylacyl)benzotriazoles

Abstract

A convenient route for efficient conversion of unprotected anthranilic acids into the corresponding N-(2-aminoarylacyl)benzotrazoles is described. N-(2-Aminoarylacyl)-benzotrazoles have been successfully used to synthesize primary, secondary and tertiary anthranilamides in high yields (71-96%).

Trichloroacetimidate-Triggered Expeditious and Novel Synthesis of N-Acylbenzotriazoles

“…The approaches are commonly characterized by two archetypal pathways. The first involves carbonyl activation (where, BtH is added to activated carboxylate), which mainly comprises activators such as I2/PPh3, NBS/PPh3 or TCT/PPh3 ; [19][20][21][22] EDC or DCC 23 along with tosyl chloride 24 and BtH with or without base. Alternatively, activation of benzotriazole involves a carboxylic acid being added to the activated BtH).…”

Temperature-controlled synthesis of N-acyl anthranilamides and quinazoline-4-ones via Pd-catalysed cascade consisting of isocyanide insertion

“…[10][11][12][13][14][15][16][17][18] Due to the exhibition of a number of biological activities and part of a number of natural products, the development of new methods for the synthesis of N-acyl anthranilamide and quinazoline-4-one skeleton have grabbed lot of attention in recent years. [19][20] In general, we use anthranilic acids for synthesizing corresponding anthranilamide, although, this process is inherently restricted by the limited range of commercially available anthranilic acids. 21 Additionally, various methods have been reported for the synthesis of N-acyl anthranilamide and quinazoline-4-one skeleton in recent years (Scheme 1).…”

One-pot synthesis of quinazolin-4(3H)-ones and2,3-dihydroquinazolin-4(1H)-ones utilizingN-(2-aminobenzoyl)benzotriazoles

“…N -(2-Aminobenzoyl)benzotriazoles are versatile reagents that are stable in crystalline form and easy to prepare and handle. These compounds have excelled as ideal synthetic auxiliaries in the synthesis of anthranilic acid amides [53], esters-thioesters [54], and heterocycles [55][56][57]. Their synthetic utility was recently shown in the preparation of 2-substituted quinolone-3-carboxylates and 4-hydroxyquinoline-2,3-dicarboxylates [56].…”