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Advancing the Morita–Baylis–Hillman Chemistry of 1‐Formyl‐β‐carbolines for the Synthesis of Indolizino‐indole Derivatives
Author(s) -
Singh Virender,
Hutait Samiran,
Batra Sanjay
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000322
Subject(s) - chemistry , dabco , baylis–hillman reaction , adduct , indole test , yield (engineering) , pericyclic reaction , stereochemistry , medicinal chemistry , carboxylate , halogenation , organic chemistry , catalysis , materials science , metallurgy
The chemistry of the Morita–Baylis–Hillman adducts of 1‐formyl‐β‐carbolines has been extended for obtaining indolizino‐indole derivatives which mimic the harmicine and homofascaplysin frameworks. Adducts of N ‐substituted methyl 1‐formyl‐9 H ‐β‐carboline‐3‐carboxylate yield indolizino‐indole derivatives upon bromination followed by aqueous workup. On the other hand, N ‐substituted 1‐formyl‐9 H ‐β‐carbolines give rise to similar products in a one‐pot DABCO‐promoted reaction of activated alkenes. Alternatively, the DMAP‐mediated Morita–Baylis–Hillman reaction of N ‐substituted methyl 1‐formyl‐9 H ‐β‐carboline‐3‐carboxylate with cycloalkenones yields adducts that cyclize intramolecularly in the presence of PBr 3 to yield compounds with the homofascaplysin framework. In contrast, the DMAP‐mediated reaction of N ‐substituted 1‐formyl‐β‐carboline with cyclohexenone directly gives a product with similar framework in a single step.