Crystal Structure of 1-(4-Chlorophenyl)-2-(5H-phenanthridin-6-ylidene)ethanone

Mehrabi, Hossein; Loghmani-Khouzani, Hossein; Sadeghi, Morteza; Charmant, Jonathan P. H.; Gunter, Charles M. M.; Ghorbani, Mohammad

doi:10.2116/analscix.23.x161

Cited by 1 publication

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“…According to the literature [ 55 ], as well as the Cambridge Structural Database, there is a plethora of compounds with an intramolecular N–H···O=C contact like 1a ; on the other hand, the family of structurally related 1,2-dihydroquinolines [ 56 ] and ethanones [ 57 ] is limited to only seven examples. In the structure of 1a , some extent of π-electron delocalization is reflected in slight shortening of the formal single bond between C1 and C2 atoms, on the contrary to a slight elongation of C2–C3 and C1–O1 distances – formally the double bonds (for crystal data see Supporting Information File 1 , pages S27 and S28), similarly to the situation found for peptide type of bonding [ 55 ].…”

Section: Resultsmentioning

confidence: 99%

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

Doušová¹,

Horák²,

Růžičková³

et al. 2015

Beilstein J. Org. Chem.

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Summary2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.

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