Fused‐Skeleton Saturated Six‐Membered 1,3‐N,O, N,N and N,S Heterocycles. Fused‐Skeleton Aryl‐Substituted Saturated Isoindolones

Abstract

In the introduction, a brief survey is given of the main types of fused-skeleton saturated six-membered 1,3-heterocycles serving as model compounds in our earlier investigations and as starting compounds in the present studies. The synthesis and conformational analysis of aryl-substituted fused-skeleton saturated 1 ,boxazines and of aryl-substituted hetero-condensed saturated isoindolones are treated. cis-trans isomerization in the saturated isoindolone moiety of the resulting tricyclic, tetracyclic and pentacyclic systems is discussed in connection with the ring-closure reactions of cis-and trans-1 ,Zdisubstituted 1,2-and 1,3-difunctional alicyclic compounds to give alicycle-fused six-membered 1,3-heterocycles. The cycloaddition reactions of dihydro-1,3 and 3,l-oxazines and the conformations of the alicycle-fused tetrahydrooxazine-azetidinone derivatives obtained are presented. Methods are given for the preparation of saturated thiazolo-and thiazino[2,3-b]quinazolinones. Unambiguous, mainly one-pot syntheses for the preparation of 1,3-heterocycles by a retro Diels-Alder method are discussed.

Catalytic Asymmetric Synthesis of Isoindolinones

“…Some excellent reviews concerning isoindolones have been published previously . The preparation of the racemic isoindolones was reviewed in 1994 . Non‐aromatic phthalimidines have also been obtained and applied to give other enantiopure natural‐like products .…”