Preparation of a Range of NNN'N'-Tetrasubstituted 1,8-Diaminonaphthalenes

DOI: 10.1039/P19810002840

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2840 - 2847 (1981)

Update date:2022-08-03

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Authors:

Alder, Roger W.

Bryce, Martin R.

Goode, Nigel C.

Miller, Nigel

Owen, Judith

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Article abstract of DOI:10.1039/P19810002840

Alkylation of 1,8-bis(methylamino)naphthalene with difunctional reagents leads to a series of 1,5-dimethylnaphtho<1,8-bc>-1,5-diazacycloalkanes (1)-(5), to 1,5-dimethylbenzonaphtho<1,8-bc>-1,5-diazacyclononane (6), and to 1,5-dimethylnaphtho<1,8-bc>-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<1,8-bc>-1,5-diazabicyclo<3.3.1>nonane (8), naphtho<1,8-bc>-1,5-diazabicyclo<3.2.2>nonane (9), and naphtho<1,8-bc>-1,5-diazabicyclo<3.3.3>undecane (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<1,8-bc>-1,5-diazabicyclo<4,3,0>nonane (24).

Full text of DOI:10.1039/P19810002840

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