68394-64-9Relevant academic research and scientific papers
Access to Fused Pyrroles from Cyclic 1,3-Dienyl Boronic Esters and Arylnitroso Compounds
Fran?ois, Benjamin,Eberlin, Ludovic,Berrée, Fabienne,Whiting, Andrew,Carboni, Bertrand
, p. 5173 - 5182 (2020/05/18)
Complimentary to classical hydroboration and boron-Wittig reactions, a new, efficient access to cyclic 1,3-dienyl boronic esters has been developed via diene or triene metathesis. Subsequently, fused pyrroles were synthesized with a broad substrate scope
Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds
Eberlin, Ludovic,Carboni, Bertrand,Whiting, Andrew
, p. 6574 - 6583 (2015/10/06)
A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp2 boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp3 boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. 1H and 11B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence.
Multicomponent reactions in PEG-400: Ruthenium-catalyzed synthesis of substituted pyrroles
Chandrasekhar, Srivari,Patro, Vidyavathi,Chavan, Lahu N.,Chegondi, Rambabu,Grée, René
supporting information, p. 5932 - 5935 (2015/01/08)
An efficient and eco-friendly method for the synthesis of substituted pyrroles has been developed via ruthenium-catalyzed multicomponent reaction of ketone, amine, and ethylene glycol in PEG-400 as solvent medium without using any external ligand. The cat
A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds
Tripoteau, Fabien,Eberlin, Ludovic,Fox, Mark A.,Carboni, Bertrand,Whiting, Andrew
supporting information, p. 5414 - 5416 (2013/06/27)
A one-pot hetero-Diels-Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).
SYNTHESIS OF TRI- AND TETRAMETHYLENEPYRROLE DERIVATIVES FROM 2-(1-ETHOXY-2-BROMOETHYL)CYCLOALKANONES
Azzuz, A.,Sorokin, V. L.,Kulinkovich, O. G.
, p. 31 - 33 (2007/10/02)
Tri- and tetramethylenepyrrole derivatives were synthesized by treatment of the corresponding 2-(1-ethoxy-2-bromoethyl)cycloalkanones with an aqueous solution of sodium hydroxide and a methanol solution of a primary amine.The transformation proceeds th
Novel Route to 4,5,6,7-Tetrahydroindoles and Pyrroles
Nishio, Takehiko,Okuda, Norikazu,Kashima, Choji
, p. 899 - 902 (2007/10/02)
Treatment of cyclic unsaturated amides, 1,4,5,6,7,7a-hexahydro-2H-indol-2-ones 1, with Lawesson's reagent yielded unexpected products, 4,5,6,7-tetrahydroindoles 2, in moderate yield.Re
OXAZOLIDINES. 1. BASIC CATALYTIC DISPROPORTIONATION OF CYCLOHEXANOSPIRO-2-OXAZOLIDINES: SYNTHESIS OF N-SUBSTITUTED 4,5,6,7-TETRAHYDROINDOLES
Kukharev, B.F.,Stankevich, V.K.,Kukhareva, V.A.
, p. 437 - 439 (2007/10/02)
It has been shown that the basic catalytic disproportionation of cyclohexanospiro-2-oxazolidines in the presence of potasium hydroxide or sodium methylate leads to N-substituted 4,5,6,7-tetrahydroindoles with a yield of up to 73percent.The influence of the character of substituents at the nitrogen atom of oxazolidine on the course of the reaction has been established.
