反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][NH2:10])[CH:2]=1.[Na]>C1(C)C=CC=CC=1>[NH:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH2:4][CH2:5][CH2:6]1参加物
実験手順
The final step in the process of the present invention is the cyclization of compound (II) to elaborate the final product (I). This intramolecular transformation is efficiently carried out by an optimized Chichibabin-type reaction (for a discussion of Chichibabin aminations, see H. Vorbrüggen, Adv. Heterocyclic Chem., 49, 1990, 117-192). Intramolecular nucleophilic cyclizations of 3-substituted pyridylalkylamines have previously been described. Thus, treatment of 3-(3-pyridyl)propylamine with two equivalents of sodium in boiling toluene afforded 1,2,3,4-tetrahydro-[1,8]-naphthyridine in 30% yield (E. M. Hawes and H. L. Davis, J. Heterocyclic Chem., 1973, 39-42). 1,2,3,4-Tetrahydro-3-phenyl-[1,8]-naphthyridine has been similarly prepared in 54% yield (E. M. Hawes and D. G. Wibberley, J. Chem. Soc. (C), 1966, 315-321). The substrate for the Chichibabin-reaction of the present invention has two nucleophilic amino groups presenting complicating issues of regioselectivity and intramolecular vs. intermolecular reactivity.
後処理
- customThis intramolecular transformation is efficiently carried out by an optimized Chichibabin-type reaction (for a discussion of Chichibabin aminations
出典と根拠
- ORDレコード
- ord-601a743085f2488fab67910a86cd8b94
- 出典データセット
- uspto-grants-2001_07
- 特許番号
- US06262268B1
関連ノート
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