63731-38-4Relevant articles and documents
Tandem Sonogashira-Hagihara coupling/cycloisomerization reactions of ethynylboronic acid MIDA ester to afford 2-heterocyclic boronic acid MIDA esters: A concise route to benzofurans, indoles, furopyridines and pyrrolopyridines
Sakurai, Yohji
, p. 1322 - 1336 (2017/07/18)
A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.
Copper- And ligand-free heteroannulation of o-halohydroxypyridine with terminal alkynes using Pd/C catalyst: One-pot synthesis of 2-substituted furopyridines and their functionalization
Park, Hee Jung,Kim, Ji-Eun,Yum, Eul Kgun,Kim, Young Hoon,Han, And Chang-Woo
, p. 211 - 218 (2015/03/03)
Three types of isomeric 2-substituted furo[3,2-b]pyridine, furo[2,3-b]pyridine and furo[3,2-c]pyridine were prepared using Pd/C-catalyzed heteroannulation of o-halopyridinols and terminal alkynes under copperand ligand-free conditions. We also demonstrated that double functionalization yielding 2,3-disubstituted furopyridines could be achieved through heteroannulation followed by bromination and Suzuki/Heck reactions. In addition, the use of recoverable Pd/C in the absence of a cocatalyst and ligand can aid in the development of greener chemical processes.
Synthesis and reactivity of aryl(alkynyl)iodonium salts
Dixon, Luke I.,Carroll, Michael A.,Gregson, Thomas J.,Ellames, George J.,Harrington, Ross W.,Clegg, William
, p. 2334 - 2345 (2013/05/21)
The first practical, yet simple, preparation of aryl(alkynyl)iodonium trifluoroacetate salts is described. The generic nature of this synthetic method has allowed the production of a range of aryl(alkynyl)iodonium trifluoroacetate salts with independent variation of both the alkynyl and aryliodo groups in yields of 30-85 %. Application of these new reagents to the synthesis of a series of 2-arylfuro[3,2-c]pyridines (40-64 %) highlights the potential of this class of materials as precursors to bioactive heterocyclic structures. These experiments have also demonstrated that, in this case, the effect of the aryliodo group on the reaction is negligible.
Synthesis of 2-arylfuro[3,2-c]pyridines and their derivatives
Krutosikova, Alzbeta,Sleziak, Robert
, p. 1627 - 1636 (2007/10/03)
A series of 2-arylfuro[3,2-c]pyridines was synthesized. 3-(5-Aryl-2-furyl)propenoic acids 1a-1h were converted to the acid azides 2a-2h, which in turn were cyclized to give 2-arylfuro[3,2-c]pyridine-4(5H)-ones 4a-4h by heating in Dowtherm. The pyridones 4a-4f were aromatized with phosphorus oxychloride to the 2-aryl-4-chlorofuro[3,2-c]pyridines 5a-5f, which were reduced with zinc and acetic acid to the title compounds 6a-6f. Reacted with phosphorus(V) sulfide, the pyridones 4a-4f yielded the corresponding thiones 7a-7f.
CONDENSED HETEROAROMATIC RING SYSTEMS. VII. SYNTHESIS OF THIENOPYRIDINES, THIENOPYRIMIDINES, AND FUROPYRIDINES FROM o-SUBSTITUTED N-HETEROARYLACETYLENES
Sakamoto, Takao,Kondo, Yoshinori,Watanabe, Ryo,Yamanaka, Hiroshi
, p. 2719 - 2724 (2007/10/02)
The cross-coupling reaction of 2-chloro-3-iodo- and 4-chloro-3iodopyridines with phenylacetylene in the presence of dichlorobis(triphenylphosphine)palladium occured at the 3-position.The 3-ethynylpyridines containing an adjacent chloro group were converti
