Coupling Isocyanide-Based
Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution
Processes
Luca Banfi*, Renata Riva*, Andrea Basso Department of Chemistry and Industrial
Chemistry, University of Genova, via
Dodecaneso 31, 16146 Genova, Italy Fax: +39(010)3536118; e-Mail: banfi@chimica.unige.it; e-Mail: riva@chimica.unige.it;
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Publikationsverlauf
Received
17 July 2009 Publikationsdatum: 30. November 2009 (online)
This account summarizes the results of studies carried out by
the authors during the last 10 years aimed at expanding the utility
of the venerable Passerini and Ugi reactions. Particular emphasis
is given to efforts that focus on coupling these processes with post-condensation,
intramolecular, aliphatic nucleophilic substitution and acyl nucleophilic
substitution reactions. The methodologies developed in these investigations
serve as the basis for short sequences for the preparation of a
diverse number of interesting drug-like structures.
1 Introduction
2 Aliphatic Nucleophilic Substitution
2.1 Two Additional Functions: Mitsunobu or Mitsunobu-like Reactions
2.2 One Additional Function: Ketopiperazines, β-Lactams
and More
64 Secondary amides are also obtained
when hydrazoic acid or its derivatives are used as substitutes of
the carboxylic acid. Using β-sulfonyloxyisocyanides as
inputs in this modified Ugi reaction, in situ intramolecular nucleophilic
substitution of the sulfonate by the secondary amine leads to tetrazolo-piperazines: Umkehrer M.
Kolb J.
Burdack C.
Ross G.
Hiller W.
Tetrahedron Lett.
2004,
45:
6421
67bWyatt PG.
Allen MJ.
Borthwick AD.
Davies DE.
Exall AM.
Hatley RJD.
Irving WR.
Livermore DG.
Miller ND.
Nerozzi F.
Sollis SL.
Szardenings AK.
Bioorg.
Med. Chem. Lett.
2005,
15:
2579
73bBelvisi L.
Bernardi A.
Colombo M.
Manzoni L.
Potenza D.
Scolastico C.
Giannini G.
Marcellini M.
Riccioni T.
Castorina M.
LoGiudice P.
Pisano C.
Bioorg. Med. Chem.
2006,
14:
169
Banfi, L.; Basso, A.; Cerulli, V.;
Guanti, G.; Lecinska, P.; Riva, R. IV Int.
Conference on ‘Multi-Component Reactions and Related Chemistry’,
Ekaterinburg: Russia, 24-28/5, 2009,
S 3.
Banfi, L.; Basso, A.; Cerulli, V.;
Guanti, G.; Riva, R. IV Int. Conference on ‘Multi-Component
Reactions and Related Chemistry’, Ekaterinburg: Russia,
24-28/5, 2009, S 16.
Banfi, L.; Basso, A.; De Moliner,
F.; Guanti, G.; Petricci, E.; Riva, R.; Taddei, M. IV
Int. Conference on ‘Multi-Component Reactions and Related
Chemistry’, Ekaterinburg, Russia, 24-28/5, 2009, PS 5.