849587-90-2Relevant academic research and scientific papers
Synthesis and reactivity of a novel class of long-lived ammonium ylides: Derivatives of benzo[b]pyrrolo[2,1-f][1.6]naphthyridine
Voskressensky, Leonid G.,Vorobiev, Ilya V.,Borisova, Tatyana N.,Varlamov, Alexey V.
, p. 4596 - 4601 (2008/09/21)
(Chemical Equation Presented) Reaction of 10-cyanotetrahydrobenzo[b][1,6] naphthyridines (1-6) with activated alkynes affords stable benzo[b]pyrrolo[2,1- f][1,6]naphthyridine-4-ium ylides (7-14) in moderate yields. A proposed mechanism for their formation consists of a new tandem multistage process.
Tandem transformations of 10-substituted tetrahydrobenzo[b][1,6] naphthyridines resulted from the Michael addition of the nitrogen atom of the tetrahydropyridine fragment to the triple bond of activated alkynes
Voskressensky,Borisova,Vorob'Ev,Postika,Sorokina,Varlamov
experimental part, p. 1547 - 1558 (2009/10/01)
A reaction of 10-R-substituted tetrahydrobenzo[b][1,6]naphthyridines (R = CN, CONH2, Me) with dimethyl acetylenedicarboxylate, methyl and ethyl propiolates, and acetylacetylene has been studied. It was found that 1-acryloyl-10-cyanotetrahydrobe
Transformations of tetrahydrobenzo[b][1,6]naphthyridines and tetrahydropyrido[4,3-b]pyrimidines under the action of dimethyl acetylene dicarboxylate
Voskressensky, Leonid G.,Borisova, Tatiana N.,Kostenev, Innokenti S.,Vorobiev, Ilia V.,Varlamov, Alexey V.
, p. 1975 - 1979 (2007/10/03)
10-Cyanotetrahydrobenzo[b][1,6]naphthyridines 3, 4 undergo addition of DMAD, followed by a Stevens rearrangement of the intermediate ylide to yield methyl dioates 8 and 9. An alternative transformation sequence starts with migration of the dimethyl butenedioate anion to the carbon of the CN group, followed by the addition of 1 mol of water, to provide succinates 10 and 11. In contrast, tetrahydropyrido[4,3-b]pyrimidines 5-7 undergo a tandem cleavage process, involving one molecule of solvent. The resulting enamines are easily cleaved by strong acids, to give dihydropyrymidinylethylamines, which are scarcely available by other synthetic means.
