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By G.W. Gribble, Thomas L. Gilchrist

This quantity of development in Heterocyclic Chemistry(PHC) is the 13th annual evaluation of the literature, masking the paintings released on very important heterocyclic ring platforms in the course of 2000. during this quantity there are really good experiences. the 1st, through H. Ila, H. Junjappa and P.K. Mohanta, covers their paintings on annulation utilizing ∝-oxoketene dithioacetals, a man-made strategy that gives important routes to an impressively wide selection of fused heterocycles. the second one, by way of R. N. Warrener, is at the synthesis of fused 7-azanorbornanes. The 7-azanorbornane structural unit is integrated right into a sequence of stylish polycyclic molecules with inflexible geometry.The next chapters, prepared via expanding heterocycle ring measurement, evaluation contemporary advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.

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1~~ 1O037 ~ r l ~ MeO\ ~k-"'-CH2 -Z N" EL":N/ hydrolysis_ ~ L -] 1 E 154 153 Scheme 26 Neighbouring group attack on the N-methoxymethyl group could also involve C=C nucleophiles resulting in CNC-bond formation. Thus, reaction of the isopropylidene-bridged Nmethoxymethyl aziridine 155 with 7-isopropylidene benzonorbomadiene 38 gave an isomeric mixture of products 158 and 159, neither of which retained the N-methoxymethyl group (Scheme 27). Again formation of dipolar adducts 156 and 157 is presumed to occur first.

The aza-ACE reaction proceeded under much milder conditions (85 ~ than its oxygen counterpart (140 ~ and was more synfacially stereoselective. The initial results were reported in 1998 <98SL588> and while some newer aspects have appeared subsequently <99TL4111, 00OL721, 00OL725>, much of the work described herein is unpublished or in press. 0]PENTANES) The N-substituted aziridinocyclobutanes 28 essential as building block (BLOCK <97CC1519>) reagents for the aza-ACE reaction were produced in a two step sequence starting from cyclobutene-l,2-diesters 25 (Scheme 4).

33 The Synthesis of Fused 7-Azanorbornanes Transition state energies have been determined by computation (PM3 and AM1) for the reaction of norbomadiene 74a (X=CHa) and 7-isopropylidenenorbomadiene 74b (X is C=CMe2) with the 1,3 dipoles 23 formed from ring-opening of the N-phenyl and N-benzyl derivatives of aziridine 22 (see, Table 1). These data demonstrate the preference for formation of exo, exoisomers 75 with norbomadiene in the N-benzyl series, however the energy difference between the transition states for the N-phenyl series is much closer and accords with the drop in stereoselectivity.

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