Palladium-catalyzed cyclization of benzamides with arynes: application to the synthesis of phenaglydon and N-methylcrinasiadine.
نویسندگان
چکیده
N-Methyl or methoxy benzamides reacted with benzynes in the presence of Pd(OAc)2, organic acid and K2S2O8 in CH3CN yielding tricyclic phenanthridinone derivatives in good yields.
منابع مشابه
Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents.
Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents is described. The reaction is highly chemoselective (CN, COOEt and NO(2) groups are tolerated). The procedure was used to perform intramolecular couplings. This cyclization reaction is the key step of the total synthesis of the N-methylcrinasiadine.
متن کاملPalladium-catalyzed regio- and chemoselective ortho-benzylation of C-H bond using a functionalizable primary amide directing group: a concise synthesis of dibenzo[b,e]azepin-6-ones.
A palladium-catalyzed regio- and chemoselective direct benzylation of primary benzamides with 2-bromobenzyl bromides under a mild basic condition has been developed affording various substituted diarylmethanes in good yields. Furthermore, the directing amide group (-CONH2) was subjected to intramolecular N-arylation with the aryl bromide moiety present in diarylmethanes leading to a concise syn...
متن کاملSynthesis of isoindolinones via a ruthenium-catalyzed cyclization of N-substituted benzamides with allylic alcohols.
N-Substituted aromatic and heteroaromatic amides reacted with substituted allylic alcohols in the presence of a ruthenium catalyst, AgSbF6 and a Cu(OAc)2·H2O oxidant, affording 3-substituted isoindolinone derivatives with diverse substituents in good to excellent yields. A possible reaction mechanism involving a five-membered ruthenacycle intermediate was proposed and strongly supported by expe...
متن کاملPalladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids.
A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.
متن کاملPreparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: a practical and versatile synthesis of psilocin.
[reaction: see text] The 4-hydroxytryptamine scaffold of psilocin was successfully prepared via palladium-catalyzed cyclization of protected N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline and an appropriately substituted silyl acetylene. Removal of the protecting groups afforded psilocin in good yield.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 81 شماره
صفحات -
تاریخ انتشار 2014