Bowman, W. Russell; Bridge, Colin F.; Brookes, Philip; Cloonan, Martin O.; Leach, David C. published the artcile< Cascade radical synthesis of heteroarenes via iminyl radicals>, Computed Properties of 89324-17-4, the main research area is radical cyclization iminyl vinyl nitrile heteroarene preparation; heteroarene alkaloid tetracycle indolizinoquinolinone ring preparation; cyclization radical reaction mechanism iminyl.
A novel cascade cyclization protocol has been developed which ‘zips up’ two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin radicals yields intermediate vinyl radicals which undergo 5-exo cyclization onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclization (or 5-exo followed by neophyl rearrangement) to yield tetracyclic π-radicals which lose hydrogen radical in an H-abstraction step. Me radicals, generated from the breakdown of trimethylstannyl radicals, are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesize the tetracyclic rings A-D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogs of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2′,3′:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).
Journal of the Chemical Society, Perkin Transactions 1 published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation) (tetracyclic). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Computed Properties of 89324-17-4.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts