Sodium → 1,2,3,4-Tetrahydro-1,8-naphthyridine

HRID 1385484

반응식

HRID 1385484 반응식
[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

참가 물질

4

반응물 2

HCID 5360545SodiumHCID 135575233-(Pyridin-3-yl)propan-1-amine

생성물 1

HCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridine수율 30%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  1. customThis intramolecular transformation is efficiently carried out by an optimized Chichibabin-type reaction (for a discussion of Chichibabin aminations

출처 및 근거

ORD 기록
ord-601a743085f2488fab67910a86cd8b94
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262268B1

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