- Preparation of a Range of NNN'N'-Tetrasubstituted 1,8-Diaminonaphthalenes
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Alkylation of 1,8-bis(methylamino)naphthalene with difunctional reagents leads to a series of 1,5-dimethylnaphtho-1,5-diazacycloalkanes (1)-(5), to 1,5-dimethylbenzonaphtho-1,5-diazacyclononane (6), and to 1,5-dimethylnaphtho-1,5-diaza-8-oxacyclodecane (7).A variety of attempts to develop a selective preparation of 1,8-bis(methylamino)naphthalene was reported.The preparation of 9,9-dimethylnaphtho-1,5-diazabicyclononane (8), naphtho-1,5-diazabicyclononane (9), and naphtho-1,5-diazabicycloundecane (10) from 1,8-diaminonaphthalene are described.Reaction of appropriate 1,4- and 1,5-dihalides with 1,8-diaminonaphthalene leads to 1,8-bis-(1-pyrrolidinyl)naphthalene (11), 1,8-bis(1,3-dihydroisoindol-2-yl)naphthalene (12), 1,8-bis-(1-piperidinyl)naphthalene (13), and 1,8-dimorpholinonaphthalene (14).Nitration of 2,7-dimethylnaphthalene gives a mixture from which 2,7-dimethyl-1,8-dinitronaphthalene may be isolated; this is reduced and alkylated to give 1,8-bis(dimethylamino)-2,7-dimethylnaphthalene (15). 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene (16) and 1,8-bis(diethylamino)-2,7-dimethoxynaphthalene (17) are similarly prepared by reduction and alkylation of 1,8-dinitro-2,7-dimethoxynaphthalene.Reaction of 2,2-dimethyl-1,3-dihydroperimidine with αα'-dibromo-o-xylene led, surprisingly, to (12) and 5-(2-propyl)benzonaphtho-1,5-diazabicyclononane (24).
- Alder, Roger W.,Bryce, Martin R.,Goode, Nigel C.,Miller, Nigel,Owen, Judith
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p. 2840 - 2847
(2007/10/02)
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