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By G.W. Gribble, Thomas L. Gilchrist

This quantity of development in Heterocyclic Chemistry(PHC) is the 13th annual assessment of the literature, protecting the paintings released on very important heterocyclic ring structures in the course of 2000. during this quantity there are really good studies. the 1st, by way of H. Ila, H. Junjappa and P.K. Mohanta, covers their paintings on annulation utilizing ∝-oxoketene dithioacetals, an artificial procedure that offers invaluable routes to an impressively wide variety 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 included right into a sequence of stylish polycyclic molecules with inflexible geometry.The next chapters, prepared by means of expanding heterocycle ring measurement, overview contemporary advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.

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4. 04, p. 274. S. A. - I Lin in "Comprehensive Heterocyclic Chemistry", K. T. , Pergamon Press, Volume 6, Part 4B, Ch. 16, pp. 48-50 and 114-120. S. Apparao, Apurba Dutta, H. Ila, H. Junjappa Jr. Chem. Soc. Perkin Trans 1 1984, 921. G. Singh, H. Ila, H. Junjappa, Tetrahedron Lett. i984, 25, 5095. J. N. Vishwakarma, S. Apparao, H. Ila, H. Junjappa Indian J. Chem 1985, 24B, 466. C. V. Asokan, H. Ila, H. Junjappa Synthesis 1985, 163. A. R. Katritzky, K. Akutagawa, J. Chem. Soc. 1986, 108, 6808. M.

Me~RI"~ ? ~ V I ~ S ~ . 35 SMe ~/R2 li "T N , ,. N ~ , R,1 H 115 M ~ > ~ ~ ~ n n = 1, 2 SMe 119 (63-68) R 20 H. Ila, H. K. 13: An Efficient Synthesis of 2,3Disubstituted and Fused Benzo[a]quinolizine-4-thiones The 13-oxodithioates 120 are precursors of a-oxoketene dithioacetals 6 and are prepared in high yields by one of our published methods <82S693>. 13 was reacted with 13-oxodithioates 120 in refluxing benzene (12 h) in the presence of triethylamine the corresponding benzo[a]quinolizine-4-thiones 121 (10 examples) were formed in 45-80% overall yields <01OL229>.

C(13) ~(17, C(14, t;'~l' /C(2) I .... ~' C(16) / I C(20)~ ~ ) 0 ( 2 1 ) 0(22) 0(19) Figure 11 X-ray structure of adduct 170 In completing this survey, we report the first synthesis of an NH,NH-diazasesquinorbomane 173 has been achieved and its structure confirmed by X-ray crystallography (Figure 12). The synthesis involved addition of perfluorobut-2-yne 47 to N-Z pyrrole 166 under thermal conditions to produce the 7-azanorbomadiene 171 (Scheme 31). 02 Bn N N 172 H I N H I N 173 sealed tube, 6h; ii) 166, 14 kbar, RT, 4 d; iii) EtOH, 10% Pd/C, 30 psi, 3d Scheme 31 Further reaction of 7-azanorbomadiene 171 at room temperature with NZ pyrrole 166 under high pressure, followed by removal of the Z-protecting groups by hydrogenolysis yielded the deprotected diazasesquinorbornane 173.

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