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

“…the water or alcohol is eliminated and the initial compounds are formed [32,33,46,47]. When the 3-aroyl-substituted compounds 17 [47] and 18 [33,34] or their hydrate and alcohol adducts 47-50 [33,34] are boiled in a mixture (10:1) of dioxane and 10% HCl (0.5-1 min) or in water (5-10 min) the pyrrole ring is opened, and the keto acids 51 and 52 are formed. Oxalic acid is eliminated from the latter, and the products 15 [47] and 16 [31,33] [33,34] with methanol (with brief boiling of equimolar amounts of the reagents in dioxane) takes place both at the C (1) atom with the formation of the methyl esters of keto acids of type 52 and at the C (3a) atom with the formation of adducts of type 50 (X = NH) [33].…”

“…The corresponding pyrrole-2,3-diones 17 (X = O) and 18 (X = NH, NPh) [a]-annelated with azaheterocycles were obtained with quantitative yields from 3-methylene-3,4-dihydro-2H-1,4-benzoxazin-2-ones [31], 3-alkoxycarbonylmethylene-3,4-dihydro-1H-1,4-benzoxazin-2-ones [32], and (Z)-3-phenacylidene-3,4-dihydro-2H-1,4-benzoxazin-2-ones [33] 15 and also 1-H-and 1-phenyl-(Z)-3-phenacylidene-2-quinoxalone [33] and 3-alkoxycarbonylmethylene-and 1-phenyltetrahydro-2-quinoxalones 16 [34] with oxalyl chloride under analogous conditions [32][33][34]. Dihydro-2H-pyrano [2,3-b]quinoxalinediones 20 are formed with yields of 5-15% together with products of type 18 (X = NH, R 1 = COOAlk, where Alk = Me, Et, R 2 = H) when equimolar amounts of tetrahydroquinoxalones 19 and oxalyl chloride are boiled in chloroform [35,36] …”

“…In the case of 3-aroyltetrahydropyrroloquinoxalinetriones of type 18 [33,34] the C (3a) atom and the carbonyl group of the COAr fragment take part in reaction with the o-phenylenediamine, and as a result the products 73, containing a benzodiazepine fragment, are formed with yields of ~100% when the reagents are briefly heated in dioxane [33,46,55]. Similarly, the trione of type 18 (R = H, Ar = C 6 H 4 Me-4) [34] reacts with 2,3-diaminopyridine, leading to an almost quantitative yield of the product 74 with a pyridodiazepine fragment [56].…”

“…Similarly, the trione of type 18 (R = H, Ar = C 6 H 4 Me-4) [34] reacts with 2,3-diaminopyridine, leading to an almost quantitative yield of the product 74 with a pyridodiazepine fragment [56].…”

Synthesis of Tetrazolo[1,5-a]quinoxaline based Azetidinones ＆ Thiazolidinones as Potent Antibacterial ＆ Antifungal Agents

“…Quinoxaline ring is a part of various antibiotics such as hinomycin, levomycin, and actinoleutin that are known to inhibit growth of gram positive bacteria and are active against various transplantable tumors. [1][2][3][4][5][6][7] In addition quinoxaline derivatives are also associated with a wide spectrum of biological activities ranging from antifungal, [8][9][10] antibacterial, [10][11][12][13][14] antitubercular, 8,9,[15][16][17][18] anti-inflammatory 19,20 and analgesic.…”