Yuehchukene analogs

Nitrothiophenes as electrophiles in polar Diels-Alder reactions. Solvent effect and microwave irradiation

“…In the 1980s, studies of aromatic heterocycles such as indoles, benzofurans, pyrroles, furans, and thiophenes part of DA reactions demonstrate the viability of these systems as dienophiles. 4 More recently we have confirmed that aromatic nitroheterocyclic act as electrophiles in DA reactions. 5,6,7,8 Herein we report our findings electrophilic behaviour of nitrothiophenes when they were exposed to different dienes strongly, moderately and poorly activated, under thermal conditions, using molecular solvents and ionic liquids and in some experiences combining it with microwave irradiation.…”

Syntheses of aza-analogous iso-ergoline scaffolds using carbene mediated C–H insertion

“…10 In our case, the respective tosylhydrazone intermediates were prepared by sonication in toluene of a mixture of either aldehyde 16 or aldehyde 21 and tosylhydrazide. 11 After drying (MgSO 4 ) and filtration, the corresponding tosylhydrazones were used directly without further purification to form the diazo intermediates by deprotonation using sodium hydride followed by heating using microwave irradiation to 135 C. Further heating at 135 C led to the in situ generation of the carbene by thermal decomposition of the diazo compound. The carbene reacted selectively with CeH insertion into the piperazine fragment.…”

Antifertility agents: synthesis of yuehchukene analogues: 6β-(indol-3-yl)-9,12-dimethyl-6,7,10,11-tetrahydro-7,11-methano-5H-[b]indole and 6β-(indol-3-yl)-9,12-dimethyl-6,7,8,11-tetrahydro-7,11-methano-5H-cyclo-oct[b]indole

“…One attractive route (Scheme 1) which we had investigated was based on the intermolecular Diels-Alder reaction for the conversion of the diene (3) into (4) followed by intramolecular acylation to obtain the key tetracyclic intermediate (5). Stereoselective transformation of the ketone (5) to the abenzoate (7) via the alcohol (ti), followed by SN2 displacement of the benzoate with the indol-3-yl group and removal of the Nprotection in (8) to give the bis-indole (9) was then possible.…”