149191-61-7Relevant academic research and scientific papers
An Efficient and Scalable Synthesis of tert-Butyl (3aR,6aS)-5-Oxohexahydrocyclo penta[c]pyrrole-2(1H)-carboxylate: A Pharmacologically Important Intermediate
Bahekar, Rajesh H.,Jadav, Pradip A.,Goswami, Amitgiri D.,Shah, Hardik A.,Dave, Bhushan N.,Joshi, Darshan A.,Pethani, Jignesh P.,Patel, Dipam,Agarwal, Sameer,Desai, Ranjit C.
, p. 266 - 272 (2017/02/26)
Hexahydrocyclopentapyrrolone derivatives constitute an important class of bicycles, and it represents an essential pharmacophore for diversified pharmacological activities. A highly efficient process for the synthesis of tert-butyl(3aR,6aS)-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 1 has been developed. The improved process involves transformation of isoindole 4 to diacid 5, using an inexpensive KMnO4 mediated oxidative cleavage as a key step. The developed process was cost-effective, high yielding, kilogram scalable, and commercially viable for synthesis of 1.
Cyclic β-amino acid derivatives: Synthesis via lithium amide promoted tandem asymmetric conjugate addition-cyclisation reactions
Davies, Stephen G.,Diez, David,Dominguez, Sara H.,Garrido, Narciso M.,Kruchinin, Dennis,Price, Paul D.,Smith, Andrew D.
, p. 1284 - 1301 (2007/10/03)
The product distribution upon conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide to dimethyl-(E,E)-nona-2,7-dienedioate can be controlled to give either the cyclic 1,2-anti-1,6-anti-β-amino ester (derived from conjugate addition and i
Pyrimidine annelated heterocycles-synthesis and cycloaddition of the first pyrimido[1,4]diazepine N-oxides
Heaney, Frances,Burke, Cathriona,Cunningham, Desmond,McArdle, Patrick
, p. 622 - 632 (2007/10/03)
5-Formyl- and 5-acetyl-4-(alkenylamino)pyrimidines 5 have been prepared as precursors to novel pyrimido[1,4]-diazepine N-oxides 3. In addition to cyclisation to the targeted dipoles the substrates 5 have also been observed to form imidazopyrimidines 12 and 39 via an intramolecular Michael addition; additionally 5b has been observed to form the pyrimidoazepinone 42. Aldonitrone 3a cycloadded readily to olefinic dipolarophiles; ketodipole 3b did not share this reactivity. Both dipoles reacted with acetylenic dipolarophiles but the ensuing cycloadducts 37 were unstable; facile ring contraction of their isoxazolopyrimidodiazepine skeletons to the pteridine nucleus is noted. The structure of 37c has been determined by X-ray crystallography.
