Synthesis of 4,4-dialkoxy-3-piperidinols. Application to the synthesis of γ-acetate dehydropipecolinonitrile

Chang, Meng‐Yang; Lee, Tein‐Wei; Lin, Chung-Han

doi:10.1016/j.tet.2011.04.102

Tetrahedron

2011

DOI: 10.1016/j.tet.2011.04.102

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Synthesis of 4,4-dialkoxy-3-piperidinols. Application to the synthesis of γ-acetate dehydropipecolinonitrile

Meng‐Yang Chang

Tein‐Wei Lee

Chung-Han Lin

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Cited by 3 publications

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“…In previous studies, we have explored the synthetic application of N-benzenesulfonyl-3-bromopiperidin-4-one (4) to generate the structural framework of 4,4-dialkoxy-3-piperidinol 5 with a range of sodium alkoxides (Scheme 2). 16 Furthermore, treatment of compound 4 with 1,2-diaminobenzene in acetic acid gave compound 3b in 61% yield. The total yield of the two-step protocol was 50%.…”

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Synthesis of Quinoxaline Analogues

Chang¹,

Lee²,

Hsu³

et al. 2011

Synthesis

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Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the a-bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting a-bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3¢-diaminobenzidine.Quinoxaline heterocycles are important benzoheterocycles in combinatorial drug discovery libraries. 1 There are a number of processes available to generate the structural skeleton of quinoxalines, but they are generally synthesized by the condensation of 1,2-dicarbonyls with 1,2-diamines in either acetic acid or ethanol heated to reflux. 2 Some recent reactions of 1,2-diaminobenzene with a-dicarbonyl equivalents are described as follows: (1) epoxides in the presence of Bi(0) and acid derivatives, 3 (2) ketones and potassium hydroxide in PEG 400, 4 (3) a-bromo ketones in an aqueous media system 5 or by use of solid phase chemistry, 6 (4) hydroxylimino ketones under microwave irradiation, 7 (5) a-hydroxyketones 8 by the use of iodine, 9 sulfamic acid, 10 nanoparticles, 11 metal complexmediated tandem oxidation process, 12 and other notable approaches. 13 Although a great number of quinoxalines and their derivatives with this specific substitution pattern have been developed, new methods for their preparation are needed. Since the above-mentioned procedures are almost all multi-step reactions, we wanted to explore a onepot methodology 14 for the preparation of tricyclic or tetracyclic quinoxaline skeletons by the a-bromination of cyclic ketones with N-bromosuccinimide (NBS) in acetic acid, followed by the addition of different aryl-1,2-diamines (e.g., 1,2-diaminobenzene; 3,4-diaminopyridine or 3,3¢-diaminobenzidine).Recently, Yao et al. reported that NBS (10 mol%) promoted the synthesis of 1,5-benzodiazepine 2 through the reaction of cyclohexanone (1a; 4.0 mmol) with 1,2-diaminobenzene (1.0 mmol) either at r.t. or at 40°C under solvent-free conditions. 15 Three components were added almost simultaneously for the one-pot reaction. However, our concise synthesis of quinoxaline 3a with the ordinal addition sequence was achieved from the reaction of cyclohexanone (1a; 1.0 mmol) with NBS (1.05 mmol) in acetic acid (5 mL), followed by the addition of the resulting a-bromo ketone with 1,2-diaminobenzene (1.1 mmol), as shown in Scheme 1. The major difference between the construction of the two frameworks of benzodiazepine 2 and quinoxaline 3a 8b is the sequence of addition of the reagents [NBS, cyclohexanone (1a), then 1,2-diaminobenzene].

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Synthesis of Quinoxaline Analogues

Chang¹,

Lee²,

Hsu³

et al. 2011

Synthesis

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Synthesis of (3‐N‐substituted‐piperidin‐4‐ylidene)acetic Acid Ethyl Esters

Chang

Lee

2012

J Chinese Chemical Soc

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A convenient preparation of skeletons 2A and 2B (cyclic γ,δ‐diamino‐α,β‐unsaturated esters) is reported by a three‐step synthetic route based on a sequence of NBS‐mediated one‐pot α‐bromination/Wittig olefination of piperidin‐4‐one 3, nucleophilic addition with NaN3, and followed by PPh3‐promoted Staudinger reduction/substitution or CuI‐catalyzed Huisgen 1,3‐dipolar cycloaddition.

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Synthesis of tetrahydro-3-benzazepines

et al. 2012

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Synthesis of 4,4-dialkoxy-3-piperidinols. Application to the synthesis of γ-acetate dehydropipecolinonitrile

Cited by 3 publications

References 38 publications

Synthesis of Quinoxaline Analogues

Synthesis of Quinoxaline Analogues

Synthesis of (3‐N‐substituted‐piperidin‐4‐ylidene)acetic Acid Ethyl Esters

Synthesis of tetrahydro-3-benzazepines

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