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A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐ a ]isoindole Enantiomers
Author(s) -
Fekete Beáta,
Palkó Márta,
Mándity István,
Haukka Matti,
Fülöp Ferenc
Publication year - 2016
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.201600434
Subject(s) - isoindole , chemistry , enantiomer , norbornene , stereochemistry , domino , ring (chemistry) , salicylaldehyde , azulene , organic chemistry , catalysis , polymer , monomer , schiff base
A simple method was developed to prepare pyrimido[2,1‐ a ]isoindole derivatives by using di‐ endo ‐ and di‐ exo ‐ethyl 3‐aminobicyclo[2.2.1]hept‐5‐ene‐2‐carboxylate enantiomers as chiral sources. The method is based on a domino ring‐closure reaction of norbornene 2‐aminohydroxamic acid followed by microwave‐induced retro‐Diels–Alder reaction. In the case of enantiomeric starting substances, the chirality is transferred from norbornene derivatives to pyrimido[2,1‐ a ]isoindoles. The configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy [based on 2D NOE cross‐peaks and 3 J H,H coupling constants] and X‐ray crystallography.