219794-68-0Relevant academic research and scientific papers
Synthesis of 10,11-didehydro- and 10,11-dihydro-quincorine and of the quincoridine analogs: Functionalized and enantiopure 1-azabicyclo[2.2.2]- octanes with four stereogenic centers
Schrake, Olaf,Braje, Wilfried,Hoffmann,Wartchow
, p. 3717 - 3722 (1998)
The convenient synthesis of 10,11-didehydro-QCI (2) and of 10,11- didehydro-QCD (4) as well as 10,11-dihydro-QCI (5) and 10,11-dihydro-QCD (6) is described. Conversion of the olefinic double bond of Quincorine 1 and Quincoridine 3 into the corresponding alkynes 2 and 4 involves twofold dehydrobromination, and an important application of the solid KOH/aliquat 336 system in the key step. The structure of didehydro-QCI (2) has been elucidated by X-ray crystal diffraction. The new alkynes 2 and 4 are more polar and more basic than QCI and QCD, respectively.
Cross-coupling reactions in Cinchona alkaloid chemistry: Aryl-substituted and dimeric quinine, quinidine, as well as quincorine and quincoridine derivatives
Frackenpohl, Jens,Braje, Wilfried M.,Hoffmann, H. Martin R.
, p. 47 - 65 (2001)
Cross-coupling reactions of modified Cinchona alkaloids provide access to a wide variety of novel arylated and dimeric derivatives of quinine and quinidine containing a single and double 1,2-amino alcohol functionality. Sonogashira and Heck reactions allow functionalization of ethynyl and 11-iodovinyl precursors. The role of bystander functionality is investigated.
Synthesis of new quinuclidine derivatives via Pd-mediated cross-coupling and cross-benzannulation reactions
T?t?s, Stefania,Fild, Manfred,Th?ne, Carsten,Grosu, Ion
scheme or table, p. 6226 - 6235 (2011/03/20)
New functionalized quinuclidines were prepared via palladium-catalyzed addition reactions of terminal alkynes (donors) to internal alkynes (acceptors). The enantiopure terminal alkynes were derivatives of quincoridine and quincorine, two semi-natural Cinc
Synthetic and structural studies of PdII and PtII complexes with quincorine and quincoridine derivatives
Fild, Manfred,Thoene, Carsten,Toetoes, Stefania
, p. 749 - 761 (2007/10/03)
A series of PdII-quincorine and -quincoridine complexes in which the ligands are coordinated through N,O-donor atoms have been synthesised, and their structural features determined by X-ray crystallography. Additionally, new chiral tetradentate N,P-ligands containing two quinuclidine cores bridged through a cis-enediyne fragment have been obtained. The different coordinating properties of the new ligands, which contain two soft phosphorus and two hard nitrogen donors, to PdII and PtII are emphasised. Several typical complexes were structurally characterised by X-ray crystallography. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
