7344-61-8Relevant academic research and scientific papers
Confirmation of the Revised Structure of Samoquasine A and a Proposed Structural Revision of Cherimoline
Dhoro, Francis,Parkin-Gibbs, Jesse,McIldowie, Matthew,Skelton, Brian W.,Piggott, Matthew J.
, p. 1658 - 1665 (2018/08/04)
The identity of the natural product samoquasine A has remained obscure since its isolation from custard apple seeds in 2000. One of the proposed structures, benzo[f]phthalazin-4(3H)-one, was prepared in two steps by regioselective ortho-lithiation/formylation of N,N-diisopropyl-2-naphthylamide, followed by cyclization with hydrazine, but was shown to be different from the natural product. Perlolidine, another candidate structure, was synthesized by a novel route involving a β-selective Heck reaction of butyl vinyl ether. Both perlolidine and samoquasine A are converted by trimethylsilyldiazomethane into the same N-methyl derivative. In addition, the 13C NMR spectra of perlolidine and another structurally mis-assigned natural product, cherimoline, are almost identical. Thus, both samoquasine A and cherimoline are actually perlolidine.
Synthesis of the grass alkaloid perlolidine through a pyridyne cyclisation reaction
Kessar,Singh
, p. 1129 - 1131 (2007/10/03)
A synthesis of the grass alkaloid perlolidine is described in which the key step involves the pyridyne cyclisation of 2-benzyloxy-5-bromo-3-[(N-phenyl) aminomethyl] pyridine.
Synthesis of various substituted benzo[c]-2,7-naphthyridines and an approach towards the skeleton of meridine. Considerations about the effect of copper (II)oxide
Bj?rk, Patrick,Malm, Johan,H?rnfeldt, Anna-Britta,Gronowitz, Salo
, p. 237 - 253 (2007/10/03)
Derivatives of benzo[c]-2,7-naphthyridines have been prepared in good yields and in one step through the use of the Pd(0)-catalyzed cross couplings of 4-formyl- and 4-acetyl-3-pyridyltrimethylstannanes with ortho-bromoacetanilides. Perlolidine, an alkaloi
First Metalation of Aryl Iodides: Directed Ortho-Lithiation of Iodopyridines, Halogen-Dance, and Application to Synthesis
Rocca, P.,Cochennec, C.,Marsais, F.,Thomas-dit-Dumont, L.,Mallet, M.,et al.
, p. 7832 - 7838 (2007/10/02)
Metalation of iodopyridines was succesfully achieved by LDA at low temperature.In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines.This procedure was applied to 2
