66730-41-4Relevant academic research and scientific papers
Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles
Bommegowda, Yadaganahalli K.,Lingaraju, Gejjalagere S.,Thamas, Saji,Vinay Kumar, Koravangala S.,Pradeepa Kumara, Challanayakanahally S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Marilinganadoddi P.
supporting information, p. 2693 - 2695 (2013/06/05)
One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy.
Allylation of Azoles with Allyltributyltin via Unstable N-(Alkoxycarbonyl)azolium Salts
Itoh, Takashi,Hasegawa, Hiroshi,Nagata, Kazuhiro,Ohsawa, Akio
, p. 1319 - 1325 (2007/10/02)
The one-pot reactions of imidazoles with allyltributyltin in the presence of alkyl chloroformates gave 2-allyl-1,3-bis(alkoxycarbonyl)-4-imidazolines in good yields.The reactions of thiazoles and oxazoles also proceeded in a similar manner.The instability of the intermediary quaternary salts required the nucleophiles to be added simultaneously with the chloroformate.Therefore, the reaction was specific for allyltributyltin, since it doesn't react with the carbonyl group of chloroformates.The dihydro allyl adducts thus obtained were aromatized with potassium ferricyanide under basic conditions to afford the corresponding 2-allylazoles.
STEREOSELECTIVE SYNTHESIS OF VINYLBENZOTHIAZOLES AND THEIR EPOXIDES
Florio, S.,Ingrosso, G.,Ronzini, L.,Epifani, E.
, p. 3365 - 3374 (2007/10/02)
Vinylbenzothiazoles 2 were stereoselectively prepared through isomerization of allylbenzothiazoles 1.Oxiranes 5 and 8 were synthesized from 2 and 1 via cyclization of the corresponding bromohydrins 3,4,6 and 7.
REVERSIBLE ALLYLIC CONDENSATION OF METALLOALLYLS OF HETEROCYCLES: COUNTERION EFFECT
Epifani, E.,Florio, S.,Ingrosso, G.
, p. 5869 - 5878 (2007/10/02)
Metalloallyls of benzothiazole, benzoxazole and pyrimidine 2 condense with aldehydes to furnish α-regioisomers 3 and 4 or γ-regioisomer 5 depending upon the experimental conditions and the nature of the metal of 2.The allylic condensation of 2 with aldehy
Palladium-Catalyzed Coupling between Organic Halides and Organotin Compounds Involving C-N Unsaturated Bonds at the Reaction Centers
Kosugi, Masanori,Koshiba, Mamoru,Atoh, Akira,Sano, Hiroshi,Migita, Toshihiko
, p. 677 - 679 (2007/10/02)
Imidoyl chlorides were good substrates which can react with a variety of organotin compounds to give ketimines in the presence of a catalytic amount of palladium complex.Under similar conditions, C-tributylstannyl imines did not give the products except with 2-(tributylstannyl)benzothiazole, -benzoxazole, and 1-methyl-2-(tributylstannyl)imidazole.And N-tributylstannyl imines could not be utilized.
