17490-70-9Relevant academic research and scientific papers
β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans
Fernandes, Rushil,Mhaske, Krishna,Narayan, Rishikesh
, (2021/11/24)
Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.
Synthesis and properties of Z-1, 3-bis- (aryl)-4-bromo-2-buten-1-ones
Potikha,Turelik,Kovtunenko
experimental part, p. 1184 - 1189 (2010/05/18)
Bromination of 1, 3-bis(aryl)-2-buten-1-ones by N-bromosuccinimide in anhydrous carbon tetrachloride gives Z-1, 3-bis(aryl)-4-bromo-2-buten-1-ones. The effect of the nature of substituent in the benzene ring on the course of a reaction with nucleophiles h
Improved synthesis of pyrylium salts leading to 2,4-disubstituted diarylfurans via novel mechanism
Bello, Angélica M.,Kotra, Lakshmi P.
, p. 9271 - 9274 (2007/10/03)
Improved synthesis of pyrylium salts from either substituted benzoic acids or their methyl esters, and substituted acetophenone is reported en route to the synthesis of 2,4-diarylfurans. The mechanism involved in the formation of the pyrylium salt using t
A convenient regioselective synthesis of 2,4-diarylfurans
Francesconi, Iris,Patel, Alpa,Boykin, David W.
, p. 61 - 63 (2007/10/03)
A facile three step process, under mild conditions, for the synthesis of 2,4-diarylfurans with the same or different substituents on the two aryl rings, starting from benzaldehydes and acetophenones, employing Haller-Bauer type cleavage of 2-aroyl-3,5-diarylfurans is described.
2,4-bis[(4-amidino)phenyl]furans as anti-Pneumocystis carinii agents
-
, (2008/06/13)
Compounds according to the formula: STR1 wherein: R1 and R2 are each independently selected from the group consisting of H, loweralkyl, aryl, alkylaryl, aminoalkyl, aminoaryl, halogen, oxyalkyl, oxyaryl, or oxyarylalkyl; R3/sub
Formation of Furan Derivatives from Phenacyl Bromides and Sodium Telluride; Attempted Extension to Coumarin Synthesis
Padmanabhan, Seetharamaiyer,Ogawa, Takuji,Suzuki, Hitomi
, p. 2114 - 2116 (2007/10/02)
The enolates, generated from phenacyl bromides by sodium telluride, yield 2,4-diarylfurans in addition to the expected dehalogenation products.No 1,4-dicarbonyl compounds could be isolated even in the presence of excess oxidizing agent, copper(II) chloride.Condensation of 2-(methoxymethoxy)arenecarbaldehydes with ethyl bromoacetate in the presence of sodium telluride gave the expected α,β-unsaturated esters which resisted cyclization to yield the desired coumarin derivatives.Attempted intramolecular Reformatsky-type reaction of 2-(bromoacetoxy)benzaldehyde gave only 6,12-epoxy-6H,12H-dibenzo-dioxocin as the major product.
