Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Abstract

Data on methods for the synthesis of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side are reviewed. Their reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations are discussed.The chemistry of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side first evolved in the seventies, when the application of 2,3-dihydro-2,3-pyrroledione derivatives as synthetic blocks for the construction of alkaloid molecules was first demonstrated [1][2][3][4][5][6][7].It should be mentioned that up to the beginning of the nineties these annelated dihydropyrrolediones were studied almost exclusively as subjects for photoreduction and photocyclization or as dienophiles in DielsAlder reactions (for the production of intermediate compounds in the synthesis of alkaloids). A large part of these papers belong to certain groups of investigators [1][2][3][4][5]. Single reports on reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations of 2,3-dihydro-2,3-pyrrolediones annelated with azaheterocycles on the [a] side have only begun to appear comparatively recently. This region of their chemical behavior has been studied little in spite of the fact that they exhibit high reactivity toward various nucleophiles (particularly with the presence of several electron-withdrawing substituents in the rings) and generate imidoylketenes during thermolysis.In the present review we examine publications existing up to March, 2002, on methods for the production of dihydropyrrolediones condensed with azaheterocycles and their chemical transformations. The review does not include data on the chemistry of isatins and their aza analogs, which were described in [8], or data on the cycloaddition of these pyrrolediones, which have been discussed before [1][2][3][4][5][6][7][9][10][11] and were reviewed in [11].

Reactions of fused pyrrole-2,3-diones with binucleophiles

“…8,[10][11][12][13] In most studies on the interaction of pyrrolobenzoxazinetriones with binucleophiles, the initial C−N 10-23 , C−O 6,8,24 , and C−S 8,25 bonds formation occurs, and there are few studies on the formation of a C-C bond, an important structural unit of organic chemistry.…”

“…In most studies on the interactions of pyrroloquinoxalintriones with binucleophiles, the initial C−N 8,58,[61][62][63][64][65] , C−O 8 , C−S 8,25,66,67 bonds formation occurs, and there are few studies on the formation the C−C bond, which is described in this chapter. (38) with isopropyl 3-amino-3-(pyridin-3-yl)acrylate.…”

Synthesis of dispiro heteroanalogs of pyrrolizidine alkaloids: crystal and molecular structure of substituted 3',4'',5-trioxodispiro[(2'',5''-cyclohexadiene)-1''(4''H),7'-[7H]pyrrolizine-2'(3'H),2-[2H]pyrrole]-1'-carboxamide

“…pyrrole]-4,5′,5′′(1′′H)-triones D and a bridged 7′-oxa-2′,12′-diazatetracyclo [6.5.1.0 1,5 .0 8,12 ] tetradecane system E.…”

“…The annulation of a pyrrol-dione cycle with a benzoxazine fragment led to the formation of the polycarbonylic heterocyclic 1H-pyrrolo[2,1-c] [1,4]benzoxazine-1,2,4-trione system. 1,2 Nucleophilic transformations of 3-aroyl-1H-pyrrolo[2,1-c] [1,4]benzoxazine-1,2,4-triones by the action of OH-and NH-mono-and NH,NH-, NH,OH-, and NH,SH-binucleophiles are convenient methods for the synthesis of carbonyl derivatives of five-and six-membered nitrogen-containing heterocycles, ensembles of such heterocycles, and fused heterocyclic systems.…”

“…1,2 Nucleophilic transformations of 3-aroyl-1H-pyrrolo[2,1-c] [1,4]benzoxazine-1,2,4-triones by the action of OH-and NH-mono-and NH,NH-, NH,OH-, and NH,SH-binucleophiles are convenient methods for the synthesis of carbonyl derivatives of five-and six-membered nitrogen-containing heterocycles, ensembles of such heterocycles, and fused heterocyclic systems. 1,5 .0 8,12 ]tetradecane system 7,8 E, respectively (Scheme 1). During continuing studies on analogous transformations, we have now examined the reaction of pyrrolobenzoxazinetriones with a spiro heterocyclic enamine containing an additional functional amide group NH 2 -substituted 2-(3,3-dimethyl-8-oxo-2-azaspiro [4.5]deca-6,9-dien-1-ylidene)acetamides.…”