A Facile Method for the Synthesis of 6-Aryl-1-(3-Chloropropanoyl)-4-[(E)-1-(2-Furyl)Methylidene)]-1,2,3,4-Tetrahydro-3-Pyridazinones and 2-(2-Chloroethyl)-5-[α-Aracyl-β-(2-Furyl)]-(E)-Vinyl-1,3,4-Oxadiazoles

Abstract

Abstract:The 6-aryl-1-(3-chloropropanoyl)-4-[(E)-1-(2-furyl)methylidene)]-1,2,3,4-tetrahydro-3-pyridazinones (6a-d) were synthesized by the reaction of acid chloride 3 with α-aracyl(β-2-furyl)acrylic acid hydrazides (2a-d) in a high yield, one pot reaction. On the other hand, 2-(2-chloroethyl)-5-[α-aracyl-β-(2-furyl)]-(E)-vinyl-1,3,4-oxadiazoles (7a-d) were also prepared by cyclodehydration ofhydrazine derivatives (4a-d). The proposed structures of the products were confirmed by elemental analysis, spectral data and chemical evidence.

Access to Convenient Synthesis of Oxazinone and Pyrimidinone Heterocycles Derived From 2(3h)-Furanone

“…Based on their facile ring opening by nitrogen nucleophiles, these furanones were converted into acyclic products which via ring closure afforded many heterocycles viz. pyrrolones, pyridazinones, triazoles, oxadiazoles, thiazolidinones, and benzoxazinones [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] . To our knowledge, the conversion of 2(3H)-furanones into pyrimidine derivatives has not been reported.…”

Reactivity of 4-tert-Butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with Hydrazines

“…The different conditions used for this reaction in no case allowed us to obtain carbolines, although different pyrazoline and pyridazinone derivatives were isolated. Representative pyrazoline and pyridazinone derivatives are included in pharmacologically important compounds due to their anti-inflammatory, analgesic, antihypertensive, antibacterial, anticancer activity as well as inhibitors of the kinesin spindle protein (KSP) [8,9,10,11].…”

2(3H)-Furanones as synthons for polyamides of 1,3-diazines and 1,3,5-triazines

“…We identified compounds 5a-d, 6a-d, 8a-d, and 10a-d as attractive molecular scaffolds for our medicinal chemistry program since both platforms are relatively novel in the patent literature, compatible with our pharmacophore model and have relatively low starting molecular weights and calculated log P values. Over the past two decades, 2(3H)-furanones have attracted strong interest from our group [3][4][5][6][7][8], because of possible applications of the corresponding biologically active compounds [9,10]. Nitrogen heterocycles constitute an important class of natural and non-natural products many of which exhibit useful biological activity [11][12][13][14].…”

“…transformation of carbonyl groups into the corresponding C=S moieties using Lawesson's reagent [7]. As part of our previous investigation on 2-(3H)-furanones [3][4][5][6][7], the preparation of (3E)-1-acetyl-3(5-aryl-2-oxofuran-3(2H)-ylidene)-1,3-dihydro-2H-indol-2-ones 3a-d was described by one of us [8]. This was consistent to the result described by Long et alwho studied monosubstituted 3-methyleneoxindoles and detected for most of them only the E-isomer [10].…”