Novel applications of the “t-amino effect” in heterocyclic chemistry; synthesis of 5H-pyrrolo- and 1H,6H-pyrido[1,2-a][3,1]benzoxazines

Verboom, Willem; DIJK, B. G. VAN; Reinhoudt, David N.

doi:10.1016/s0040-4039(00)94316-8

Cited by 26 publications

(6 citation statements)

References 5 publications

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“…In the solvent-free syntheses, the yields and purity of the products could be considerably improved. Formation of the oxazine ring 71 was also noted [30]; similar behavior was previously observed during photochemical or thermal reactions in solution phase [55][56][57]. It should be noted that all the above-mentioned reactions took place without a catalyst.…”

Section: -100%supporting

confidence: 71%

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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: -100%supporting

confidence: 71%

“…Trifluoroacetophenones likewise cyclized to benzoxazines upon heating [55][56][57]. This reaction was recently used to modify the α-position of a dialkylamino group [99].…”

Section: -92%mentioning

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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“…Am. (41) 12aP, (4) 18aP, (9) 13P, (5) 14P, (32) 7a 6 2 16b 4.6 20 PH 2 (65) 12bP, (4) 18bP, (10) 13P, (5) 14P, (22) 7b…”

Section: Resultsmentioning

confidence: 99%

“…Part of the eliminated sulfonamide (7a) was lost. In contrast, 12bP and 12cA were not affected by A1C13/benzene (run 2) or A1C13/ anisóle (run 3) at room temperature or even at 70 °C (run 4). Compound 12cA was used as an ortho-para mixture containing some 15c.…”

Section: Resultsmentioning

confidence: 99%

“…In 1972 Meth-Cohn and Suschitzky reviewed the formation of heterocycles by ring closure of ortho-substituted tertiary anilines (the "tert-amino effect").1 We have demonstrated that this type of reaction has a wider applicability, e.g. for the synthesis of pyrrolo-and pyrido-[l,2-a]indoles, pyrrolo[l,2-a]quinolines, benzofc]quinolizines, [ 1,4]oxazino [4,3-a] quinolines,2 and pyrazinoquinolines.3 The synthesis of benzoxazines,4 benzothiazines, and a quinoxaline5 can also be regarded as examples of this type of reaction. The formation of all these compounds takes place via either a 1,5-or a 1,6-hydrogen shift, depending on the structure of the reactant.…”

Section: Introductionmentioning

confidence: 99%

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