Malonic Acid → 4H,5H-furo(3,2-c)pyridin-4-one

HRID 734300

Reaktionsgleichung

Reaktionsgleichung von HRID 734300
O=O.C1C=C(C=O)OC=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=[CH:16]C(O)=O.C(O)(=O)CC(O)=O.N1CCCCC1.O1C=CC=C1C=C[C:40]([N:42]=[N+]=[N-])=[O:41].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C(N(CC)CC)C>[O:10]1[C:11]2[CH:15]=[CH:16][NH:42][C:40](=[O:41])[C:12]=2[CH:13]=[CH:14]1

Komponenten

9

Edukt 7

HCID 867Malonic AcidHCID 977OxygenHCID 7362FurfuralHCID 8082PiperidineHCID 10876Furylacrylic acid2×HCID 199401P,P-Diphenylphosphinic azideHCID 27775243-(Furan-2-yl)-acryloyl azide2×

Produkt 1

HCID 2887464H,5H-furo(3,2-c)pyridin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

For example, in making a compound of formula I in which Y is oxygen, Scheme A can be followed. Briefly, 2-furfural (1) is converted under heating into 3-furan-2-yl-acrylic acid (2) using malonic acid and a suitable base such as piperidine. 3-(Furan-2-yl)-acrylic acid (2) is converted into 3-(furan-2-yl)-acryloyl azide (3) using DPPA and a suitable base such as triethylamine. The azide (3) was cyclized to afford 5H-furo[3,2-c]pyridin-4-one (4) upon heating and a catalytic amount of iodine. 5H-furo[3,2-c]pyridin-4-one is chlorinated on the 4th position with POCl3 to afford 4-chloro-furo[3,2-c]pyridine (5). 4-Chloro-furo[3,2-c]pyridine is treated with bromine, and subsequently with DBU to afford compound (6). The chlorine atom of compound (6) is replaced with an amino group by the action of aqueous ammonia to afford compound (7). Compound (7) is subsequently subjected to Pd(PPh3)4, sodium carbonate, R—B(OH)2 or a compound of formula R—B(OR′)2, in which the radical —B(OR′)2 can be represented as

Quellen und Nachweise

ORD-Eintrag
ord-9e4cb704e15f4e60bf531f7329505ef8
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592352B2

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