Novel synthesis of benzotriazolyl alkyl esters: an unprecedented CH₂ insertion

Abstract

Versatile synthesis of benzotriazolyl alkyl esters (BAEs) from N-acylbenzotriazoles using DCM as a methylene building block.

Organo NHC catalyzed aqueous synthesis of 4β-isoxazole-podophyllotoxins: in vitro anticancer, caspase activation, tubulin polymerization inhibition and molecular docking studies

“…18,19 Remarkably, because of their numerous biological uses, N -heterocycles with an oxygen atom are regarded as an important class of compounds in medicinal chemistry. 20 In view of this, the selection of an isoxazole ring in the design and synthesis of biologically active compounds is considered to be a better choice, since in isoxazole both O and N atoms are present in adjacent positions and have low bond dissociation energy. 21 Also, isoxazole consists weak basic character and due to a weak N–O bond, this ring breaks simply by photolysis and thermolysis.…”

Synthesis of 5-aryl-3,3′-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles via sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions

“…Methylenation is a well-known structural modification reaction in organic synthesis. 3 Lewis acid-mediated synthesis of 3,3′-bis-7-azaindolylmethane derivatives using zinc- or acid-mediated cross-coupling reaction of 7-azaindoles with a number of diverse aldehydes provides the corresponding C3-linked methylenation products is reported. 4 However, the development of the synthesis of 3-methylenation products of indoles and 7-azaindoles by green chemistry protocol using a catalyst-free, aqueous, and microwave irradiation method would be an alternate and efficient method warranted.…”

Synthesis of N-acylbenzotriazole using acid anhydride

“…[4][5][6] In neutral and mild conditions, N-acylbenzotriazoles are the most dependable and reliable substitute for acid chlorides to achieve esters, peptides, amides, acid azides, diketones, oxazolines and, thiazolines via N-, O-, S-, and C-acylations. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] It has also been used for the synthesis of tetrazole, urea, carbamate, and thiocarbamates via Curtius rearrangement. 23,24 Interestingly, the benzotriazole ring cleavage (BtRC) chemistry is proven to have a pivotal role in the synthesis of N-phenylamides and benzoxazoles.…”