Tetrahedron p. 7663 - 7678 (1992)
Update date:2022-09-26
Topics:
Golka
Keyte
Paddon-Row
The synthesis of some novel 1,4-dimethoxynaphthalene-bridge-heterocycle systems is described. In these systems, the naphthalene and heterocyclic groups are fused to a rigid bridge consisting of linearly fused norbornyl and bicyclo[2.2.0]hexyl groups. Bridges used herein have relays of 2-, 4-, and 6-bonds long. The heterocycle is either 3,6-di(2'-pyridyl)-pyridazino, or pyrido and was attached to the bridge by annulation methods. The pyridazine systems, 2(m,n), were synthesized via Diels-Alder reaction of 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine with the alkenes, 13 and 6(m,n), and subsequent aromatization of the adducts with DDQ. Pyridine annulation was successfully carried out using two different methods: (i) Boger pyridine annulation of ketones, 11, 20b, and 21b, (with 1,2,4-triazine and pyrrolidine): (ii) Diels-Alder reaction of alkenes 13 and 6(m,n) with 3-thiomethyl-1,2,4-triazine, followed by Raney nickel reductive desulfurization of the aromatized adducts. The synthesis of Ru(II)(2,2'-bipyridyl)2 complexes of the pyridazino systems 9(m,n) and 10, is also described.
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Doi:10.1016/S0040-4039(00)61781-1
(1992)Doi:10.1016/j.chempr.2018.01.017
(2018)Doi:10.1016/S0040-4039(00)79004-6
(1992)Doi:10.1021/jo00055a011
(1993)Doi:10.1016/S0040-4039(98)02429-0
(1999)Doi:10.1039/c39920001723
(1992)