Thermal Isomerization of 4-Amino-3-vinylpyridines: Synthesis of Fused 1,6-Naphthyridines and Unexpected New ”tert-Amino Effect” Cyclization to Azepines

Ojea, Vicente; Muinelo, I.; Figueroa, Michelle; Ruiz, Marı́a; Quintela, José M.

doi:10.1055/s-1995-5024

Cited by 16 publications

(4 citation statements)

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“…It is not only tertiary anilines with an ortho-vinyl group that can be cyclized by the mechanism of the tert-amino effect. The cyclizations of tertiary amines of pyridine 13 have been described [18,19]. We consider it necessary to mention two unexpected paths of ring closure that emphasize the important role of the tertiary amino group in cyclization by the mechanism of the tert-amino effect.…”

Section: Reinhoudt Reactionmentioning

confidence: 99%

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tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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The term "tert-amino effect" was proposed in 1972 [1] for the cyclization reactions of tertiary anilines containing various double bonds at the ortho position. Meth-Cohn and Suschitzky [1] referred to the first observation of the tert-amino effect by Pinnow in 1895 [2]. Many different examples of reactions involving the tert-amino effect have now accumulated, and it clearly is a convenient method for the synthesis of an impressive number of nitrogen-containing heterocycles that otherwise might be difficult to obtain. Reviews were published by Reinhoudt in 1990 [3] and by Meth-Cohn in 1996 [4] on heterocyclization reactions that take place by the mechanism of the tert-amino effect. Another review dedicated to 1,6-and 1,8-naphthiridine derivatives was published in 2003 by Quintela [5]. In the review [6] that we published in 2005, attention was focused on the use of such reactions for the synthesis of spiro compounds. In the review [7], published in 2006, the cyclization reactions of ortho-vinylanilines and their heterocyclic aza analogs were considered, and classification according to the method of ring formation was proposed.

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Section: Reinhoudt Reactionmentioning

confidence: 99%

“…The second example describes ring closure in the 4-amino-3-vinylpyridine derivatives 17, obtained from 3-bromopyridine-4-carbaldehyde [19]. It was shown that cyclization of the piperidine derivative 17a led to the expected product 18a.…”

Section: Reinhoudt Reactionmentioning

confidence: 99%

tert-Amino effect: the Meth-Cohn and Reinhoudt reactions (Review)

Platonova

Глухарева

Zimovets

et al. 2013

Chem Heterocycl Comp

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“…In conclusion, we are aware of only one other report (other than a patent application related to this work) wherein pyridines were utilized in the T-reaction to afford a tetrahydronaphthyridine scaffold . Examples of the T-reaction with other heterocycles have included quinolines, pyrazoles, pyridazines, indoles, and uracils .…”

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confidence: 99%

Synthesis of a Tetrahydronaphthyridine Spiropyrimidinetrione DNA Gyrase Inhibiting Antibacterial Agent - Differential Substitution at all Five Carbon Atoms of Pyridine.

et al. 2014

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The synthesis of (-)-1, a potent antibacterial agent, was achieved stereoselectively in nine steps from readily available starting materials. Directed metalations were developed to assemble a pentasubstituted pyridine with appropriately positioned aldehyde and dimethylmorpholine substituents for a key tertiary amino effect reaction (T-reaction) that led to the spirocylic architecture. Ultimately, (-)-1 was isolated as the thermodynamically most favored stereoisomer.

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“…N,N-Dialkylanilines having an ortho-vinyl substituent also exhibit the same type ring closure reactions [ 15 , 16 , 17 , 18 , 19 , 20 ]. These reactions provide an original way to form C-C bonds by insertion into a virtually non-activated NCH 2 group [ 21 ].…”

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confidence: 99%