Synthesis and Properties of Azomethines from α‐Amino‐N‐heterocycles. Synthesemöglichkeiten unter besonderer Berücksichtigung der Staudingerschen Iminophosphoranmethode

Bödeker, Jürgen; Courault, K.

doi:10.1002/prac.19803220222

Cited by 18 publications

(3 citation statements)

References 17 publications

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“…22 The compound was prepared from 3,4-dimethoxybenzaldehyde (895 μL, 6 mmol) and 2-aminopyridine (1.13 g, 12 mmol) following general procedure A. Off-white solid; 1.80 g, 89% yield; 1 1-Phenyl-N,N′-bis(2-thiazolyl)methanediamine (2d). 23 2-Aminothiazole (1.00 g, 10 mmol, 2 equiv) was added to a flask containing 3 Å molecular sieves. The flask was then purged with argon.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

NHC-Catalyzed Aza-Benzoin Condensation of N,N′-Dipyridin-2-yl Aminals with Aldehydes

2021

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α-Amino ketones are useful compounds because of their synthetic utility and bioactivities. After observing the ability of N,N′-dipyridin-2-yl aminals to form imines in situ, the synthesis of α-amino ketones using N,N′-dipyridin-2-yl aminals was proposed. Through the NHC-catalyzed aza-benzoin reaction between aromatic/aliphatic aldehydes and N,N′-dipyridin-2-yl aminals, α-amino ketones, including aromatic, heterocyclic, and aliphatic versions, were synthesized with yields up to 99%. A direct route toward N-Boc-protected α-amino ketones from N,N,N′-tris-Boc aminals was also discovered, yielding the desired N-Boc-protected α-amino ketones in yields up to 73%.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

NHC-Catalyzed Aza-Benzoin Condensation of N,N′-Dipyridin-2-yl Aminals with Aldehydes

2021

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“…For related literature, see: Boedeker & Courault (1980); Che & Wang (2007); Habibi et al (2007); Hodnett & Dunn (1970); Panneerselvam et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

“…knowledge, however, the addition products of Schiff bases are relatively less reported. In this paper, we report the synthesis and crystal structure of N-(methoxy(4-nitrophenyl)methyl)pyridin-2-amine (Boedeker et al, 1980), which is a addition product of methyl 4-nitro-N-(pyridin-2-yl)benzimidate with methanol.…”

Section: Data Collectionmentioning

confidence: 99%

N-[Methoxy(4-nitrophenyl)methyl]pyridin-2-amine

Fang

Shi

et al. 2007

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.050; wR factor = 0.131; data-to-parameter ratio = 11.7.In the title compound, C 13 H 13 N 3 O 3 , the nitro group is twisted away from the attached benzene ring by 19.5 (3) . The dihedral angle between the benzene and pyridine rings is 78.2 (1) . In the crystal structure, molecules are connected into chains along the [001] direction by N-HÁ Á ÁN hydrogen bonds. Experimental Crystal dataC 13 H 13 N 3 O 3 M r = 259.26 Monoclinic, P2 1 =c a = 10.661 (2) Å b = 14.153 (3) Å c = 9.0410 (18) Å = 110.70 (3) V = 1276.1 (5) Å 3 Z = 4 Mo K radiation = 0.10 mm À1 T = 293 (2) K 0.32 Â 0.26 Â 0.22 mm Data collection Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1998) T min = 0.969, T max = 0.979 2666 measured reflections 2500 independent reflections 1642 reflections with I > 2(I) R int = 0.026

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References

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Synthesis and Properties of Azomethines from α‐Amino‐N‐heterocycles. Synthesemöglichkeiten unter besonderer Berücksichtigung der Staudingerschen Iminophosphoranmethode

Cited by 18 publications

References 17 publications

NHC-Catalyzed Aza-Benzoin Condensation of N,N′-Dipyridin-2-yl Aminals with Aldehydes

NHC-Catalyzed Aza-Benzoin Condensation of N,N′-Dipyridin-2-yl Aminals with Aldehydes

N-[Methoxy(4-nitrophenyl)methyl]pyridin-2-amine

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