Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines—synthesis and conformational study

Csütörtöki, Renáta; Szatmári, István; Heydenreich, Matthias; Koch, Andreas; Starke, Ines; Fülöp, Ferenc; Kleinpeter, Erich

doi:10.1016/j.tet.2012.05.048

Cited by 9 publications

(3 citation statements)

References 19 publications

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“…These processes followed by ringclosing reactions led to the formation of naphth[1,2-e][1,3]oxazino [3,4-c][1,3]benzoxazines, [3,4] naphth[1,2-e][1,3]oxazino- [3,4-c]quinazolines, [5] naphth[1,2-e][1, 3]oxazino [3,4-c]quinazolin-13-ones, [6] naphth[1,2-e][1,3]oxazino [4,3-a]isoquinolinones, [7] naphth [1,3] These processes followed by ringclosing reactions led to the formation of naphth[1,2-e][1,3]oxazino [3,4-c][1,3]benzoxazines, [3,4] naphth[1,2-e][1,3]oxazino- [3,4-c]quinazolines, [5] naphth[1,2-e][1, 3]oxazino [3,4-c]quinazolin-13-ones, [6] naphth[1,2-e][1,3]oxazino [4,3-a]isoquinolinones, [7] naphth [1,3]…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives

et al. 2017

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New non‐racemic naphth[1,3]oxazino[3,2‐a]quinoxalinones have been synthesized starting from an enantiomeric hexahydroquinoxalinone and 1‐aminoalkyl‐2‐naphthols or 2‐aminoalkyl‐1‐naphthols. The enantiopure annelational analogues naphth[1,3]oxazino[3,4‐a]quinoxalinone derivatives were also synthesized from the reactions of naphthols and the non‐racemic quinoxalinone followed by a ring‐closing reaction with formaldehyde. In addition to the study of the conformational behaviour of the new heteropolycycles, the diastereoselectivity and formation of the possible diastereomers were examined by NMR analysis. Theoretical calculations were performed to confirm the experimental results.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives

et al. 2017

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“…Furthermore, 1,3-oxazine derivatives can also be used as an intermediate in the synthesis of N-substituted aminoalcohols [59]. Therefore, several methods for the synthesis of 1,3-oxazine derivatives have been reported [60][61][62][63][64][65][66].…”

Section: Introductionmentioning

confidence: 99%

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

Pelit

Turgut

2016

Journal of Chemistry

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New 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthols were obtained by condensation of 2-aminothiazole, aromatic aldehydes, and 2-naphthol in the presence of (+)-camphor-10-sulfonic acid ((+)-CSA) as an effective catalyst under ultrasound-promoted solvent-free conditions. The 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthol derivatives were converted in ring-closure reaction with formaldehyde to the corresponding naphthoxazine derivatives.

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“…Several examples have been published to extend the reaction and synthesize variously substituted aminonaphthol derivatives 12 containing analogues were reacted with a wide range of cyclic amines to furnish various aminonaphthol derivatives. These processes followed by ring-closure reactions lead to the formation of naphth [1,2-e] [1,3]oxazino [3,4-c] [1,3]benzoxazines 13,14 , naphth[1,2-e] [1,3]oxazino [3,4-c]quinazolines 15 , naphth [1,2-e] [1,3]oxazino [3,2-c]quinazolin-13-ones 16 and naphth [1,2- 17 .…”

Section: Introduction and Aimsmentioning

confidence: 99%

Synthesis and conformational analysis of novel naphthoxazine-fused polyheterocycles

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Novel piperidine-fused benzoxazino- and quinazolinonaphthoxazines—synthesis and conformational study

Cited by 9 publications

References 19 publications

Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives

Synthesis and Conformational Behaviour of Enantiomeric Naphthoxazinoquinoxalinone Derivatives

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

Synthesis and conformational analysis of novel naphthoxazine-fused polyheterocycles

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