Synthesis of phosphonate derivatives of 2,3-dihydroindene
Graphical abstract
References and notes (28)
- et al.
Tetrahedron Lett.
(1997) - et al.
Bioorg. Med. Chem.
(2002) - Oshiro, Y.; Ueda, H.; EP 173331, 1986; Chem. Abstr. 1986, 105,...
- Noda, K.; Nakagawa, A.; Yamagata, K.; Nakashima, Y.; Tsuji, M.; Aoki, T.; Ide, H. U.S. Patent 4443626, 1984; Chem....
- et al.
Pure Appl. Chem.
(2004) - et al.
Bioorg. Med. Chem. Lett.
(1995) - Neubert, T.; Kawatkar, A. S.; Martinborough, E.; Termin, A. WO/2006/133459 Patent, 2006; Chem. Abstr. 2007, 146,...
Acta Pharm.
(1999)- et al.
J. Am. Chem. Soc.
(2005) - et al.
J. Braz. Chem. Soc.
(2009)
J. Org. Chem.
Synlett
Synthesis
ARKIVOC
Cited by (13)
Novel 1,3,4-oxadiazole chalcogen analogues: Synthesis and cytotoxic activity
2022, European Journal of Medicinal ChemistryCitation Excerpt :All final compounds are >95% pure by elemental analysis on a PerkinElmer 240-B analyser, for C, H, and N, and for representative compounds, 6 and 14, by High Performance Liquid Chromatography (HITACHI Primaide HPLC, 1 mL/min flow, 90% linear gradient of solvent A (acetonitrile) in B (water)). Compound 20 was synthesized as reported in literature [32]. To a solution of ethyl acetoacetate (0.397 g, 3.1 mmol, 1.2 eq) in THF (3 mL) at 0 °C was slowly added NaH 60% in mineral oil (1.5 eq).
N-alkylpiperidine carbamates as potential anti-Alzheimer's agents
2020, European Journal of Medicinal ChemistryCitation Excerpt :N-(2,3-dihydro-1H-inden-2-yl) piperidine alcohols 52–55 were prepared in modest yields (21–33%) by alkylating the nitrogen of starting piperidines 40–43 with 2-bromo-2,3-dihydro-1H-indene (56) in the presence of K2CO3 and a catalytic amount of KI in MeCN at reflux. Bromide 56 was prepared from 2,3-dihydro-1H-inden-2-ol (57) and bromine in the presence of triphenylphosphine in CH2Cl2 [35] in 83% yield. The designed phenyl carbamates 4–15 and 4-isopropylphenyl carbamates 16–27 were synthesized in high yields (85–96%) by treating N-alkyl alcohols 44–55 with phenyl isocyanate or 4-isopropylphenyl isocyanate in the presence of a catalytic amount of N,N-dimethylpyridin-4-amine (4-DMAP) in CH2Cl2 at room temperature [36].
A substitution/dynamic kinetic resolution - Asymmetric transfer hydrogenation tandem process for preparation of stereocenters Β-hydroxy sulfones
2018, Molecular CatalysisCitation Excerpt :By screening a series of N–(4–methyl)benzenesulfonylated 1,2–diphenylethylenediamine (TsDPEN)–based η6–areneRu complexes and η5–Cp*M complexes (Cp* = pentamethylcyclopentadiene) [29–31], η6–mesityleneRuTsDPEN complex could behave efficiently as an optimal catalyst in substitution/DKR–ATH tandem process, furnishing optically pure 1,2–position stereocenters β-hydroxy sulfones with high yields, enantioselectivities (92–99% ee) and diastereomeric ratios (up to 99:1) under mild reaction conditions (shown in Scheme 1). At the outset of our research, the α–bromoindenones and 2-bromo-3,4-dihydronaphthalen-1(2H)-one were prepared according to the published procedures [32]. All other chemicals and solvents were of analytic grade and used as received except as specified.
Acetyl Bromide Promoted Sequence via Allene Intermediates: Metal-Free Construction of 2,3-Dihydroindenes and Isoindolines
2016, Advanced Synthesis and Catalysis