Fused aziridines as sources of azomethine ylides

Abstract

The use of fused aziridines as sources of azomethine ylides in the synthesis of polyheterocyclic compounds is examined. Features of thermo-and photolytic opening of aziridines and aspects of the stereo-, regio-, and chemoselectivity of cycloaddition and electrocyclization of azomethine ylides are discussed.

Oxidative Aminoaziridination of 2‐Vinylfuran Derivatives as an Approach to Hexa‐2,5‐diene‐1,4‐dione Monohydrazones

“…The former approachd oes not requiret he loss of aromaticity of the furan core, andt he employment of the resulting furyl-substituted aziridines in furthert ransformations (e.g.,C ÀNb ond cleavage, [10] 1,3-dipolar cycloaddition, [11] and electrocyclization [12] of the respective azomethine ylides) could provide easy accesst o variousf uryl-substituted compounds. The latterr eactionp athway is more unusual and attractive, as it serves as an approach to the derivatives of (2Z)-hexa-2,5-diene-1,4-dione, which are hardly accessible by extrapolating upon known methods.…”

N-(4-(6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene-2-yl)phenyl)acetamide

“…to the colored azomethine ylide form (open ring) [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. The closed-ring and open-ring forms of bicyclic aziridines exhibited absorption spectra in solution state.…”

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

“…Ring expansions of azirines ( 17 ), 18,23,47–51 cyclopropanes ( 19 ), 34,52,53 or aziridines ( 21 ) 17,54 to form azetines capture the inherent reactivity of three-membered rings to enable access to the strained azetine products (Fig. 2C).…”

“…[19][20][21][22] The synthetic utility of Dewar photoadducts is reviewed elsewhere. 23,24 Additionally, 2-azetine 8 has been found to be the product of the reaction between a recently discovered inhibitor for bacterial caseinolytic protease (ClpP) and a serine residue in the binding pocket. This product is formed when the inhibitor and the serine form a covalent bond, leading to the formation of the azetine 8 and inhibition of the ClpP enzyme.…”

“…[35][36][37][38] 2-Azetines (3) are similarly accessible by elimination of a leaving group from an azetidine (16), 40,45 which can occur in situ from an azetidine intermediate [41][42][43] or by alphadeprotonation of a 3-azetidinone followed by trapping with an electrophile. 44,46 Ring expansions of azirines ( 17), 18,23,[47][48][49][50][51] cyclopropanes (19), 34,52,53 or aziridines (21) 17,54 to form azetines capture the inherent reactivity of three-membered rings to enable access to the strained azetine products (Fig. 2C).…”