20734-57-0Relevant academic research and scientific papers
A divalent protecting group for benzoxaboroles
Vanveller, Brett,Aronoff, Matthew R.,Raines, Ronald T.
, p. 21331 - 21334 (2013)
1-Dimethylamino-8-methylaminonaphthalene is put forth as a protecting group for benzoxaboroles. The ensuing complex is fluorescent, charge-neutral, highly stable under basic conditions, stable to anhydrous acid, and readily cleavable in aqueous acid to return the free benzoxaborole. The Royal Society of Chemistry 2013.
Preparation of a Range of NNN'N'-Tetrasubstituted 1,8-Diaminonaphthalenes
Alder, Roger W.,Bryce, Martin R.,Goode, Nigel C.,Miller, Nigel,Owen, Judith
, p. 2840 - 2847 (2007/10/02)
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).
