A Critical Review of the 2000 Literature Preceded by Two by G.W. Gribble, Thomas L. Gilchrist

By G.W. Gribble, Thomas L. Gilchrist

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

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7). NMR spectroscopy allowed distinction between the isomers on the basis of symmetry. 85) in accord with that expected for a compound with C2-symmetry. It was not possible to isolate the separate atropisomers in this system since the energy barriers governing rotation were too low. More success was obtained in the NZ, NZ-diazasesquinorbomane series where it was possible to lock the N-Z isomers in conformations that were stable in solution to well above 100 ~ Thus, reaction of the N-Z 7-azanorbomadiene-2,3-anhydride 165 with N-Z pyrrole 166 yielded a single stereoisomer 167 in which the N-Z bridges were syn-facially related (Scheme 30).

Warrener 32 norbomene dipolarophiles have been uncovered in reactions with aziridine reagents, the bridge component of the dipolarophile did play a role in the stereoselectivity of the addition. A second factor also contributes to the stereoselectivity, notably the nature of the substituent on the aziridine nitrogen. 30 . . X=NPh Hs. (3 N P h + ~ O/~ 73 exo-isomer 9 Scheme 10 The stereochemical outcomes could be rationalised by reference to the two types of transition state (TSA and TSB) which arose in the attack of the 1,3-dipole onto the exo-face of the norbornene reagent (Figure 3).

Thesis, Indian Institute of Technology, Kanpur, India, 2000, p. 00TH142 142. 01JOM(624)34 H. Ila, H. Junjappa, O. Barun, J. Organomet. Chem. 2001, 624, 34. A. Roy, S. Nandi, H. Ila, H. Junjappa, Org. Lett. 2001, 3, 229. 01OL229 J. R. Suresh, U. K. Syam Kumar, H. Ila, H. Junjappa, Tetrahedron 2001, 57, 781. 01T781 94IJC501 94MI35 94TH142 25 Chapter 2 The Synthesis of Fused 7-Azanorbornanes Ronald N. 1 INTRODUCTION The medicinal value of alkaloids containing N-bridged alicyclic ring systems have been recognised for some time and exploited commercially.

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