e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Journal of heterocyclic chemistry

Furopyridines. III. A new synthesis of furo [3, 2??b] pyridine

S Shiotani, H Morita

Index: Shiotani, Shunsaku; Morita, Hiroyuki Journal of Heterocyclic Chemistry, 1986 , vol. 23, # 3 p. 665 - 668

Full Text: HTML

Citation Number: 11

Abstract

Abstract A convenient synthesis of furo [3, 2-b] pyridine and its 2-and 3-methyl derivatives from ethyl 3-hydroxypiconate (1) is described. The hydroxy ester 1 was O-alkylated with ethyl bromoacetate or ethyl 2-bromopropionate to give the diester 2a or 2b. Cyclization of compound 2a afforded ethyl 3-hydroxyfuro [3, 2-b] pyridine-2-carboxylate (3) which in turn was hydrolyzed and decarboxylated to give furo [3, 2-b] pyridin-3-(2H)-one (4a). ...

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

Ethanol Structure

~85%

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

ETHYL 3-(2-ETHOXY-2-OXOETHOXY)PICOLINATE Structure

ETHYL 3-(2-ETHO...

~91%

Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate Structure

Ethyl 3-hydroxy...

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

~%

Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate Structure

Ethyl 3-hydroxy...

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

~%

Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate Structure

Ethyl 3-hydroxy...

3-methylfuro[3,2-b]pyridine-2-carboxylic acid,ethyl ester Structure

3-methylfuro[3,...

~80%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

~%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

~%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

Ethanone,1-(3-hydroxy-2-pyridinyl)- Structure

Ethanone,1-(3-h...

~%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

ethyl 3-(methoxymethoxy)picolinate Structure

ethyl 3-(methox...

~%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

Ethanone, 1-(3-ethoxy-2-pyridinyl)- (9CI) Structure

Ethanone, 1-(3-...

~%

3-Methylfuro[3,2-b]pyridine-2-carboxylic acid Structure

3-Methylfuro[3,...

2-methyl-2,3-dihydrofuro[3,2-b]pyridin-3-ol Structure

2-methyl-2,3-di...

~90%

2-methylfuro[3,2-b]pyridine Structure

2-methylfuro[3,...

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

~%

2-methylfuro[3,2-b]pyridine Structure

2-methylfuro[3,...

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

~%

2-methylfuro[3,2-b]pyridine Structure

2-methylfuro[3,...

2-METHYLFURO[3,2-B]PYRIDIN-3(2H)-ONE Structure

2-METHYLFURO[3,...

~%

2-methylfuro[3,2-b]pyridine Structure

2-methylfuro[3,...

ethyl 2-(2-ethoxycarbonyl-3-pyridyloxy)propionate Structure

ethyl 2-(2-etho...

~%

2-methylfuro[3,2-b]pyridine Structure

2-methylfuro[3,...

Furo[3,2-b]pyridin-3-ol,2,3-dihydro-(9CI) Structure

Furo[3,2-b]pyri...

~93%

4-AZABENZO[B]FURAN Structure

4-AZABENZO[B]FURAN

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

~%

4-AZABENZO[B]FURAN Structure

4-AZABENZO[B]FURAN

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

~%

4-AZABENZO[B]FURAN Structure

4-AZABENZO[B]FURAN

Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate Structure

Ethyl 3-hydroxy...

~%

4-AZABENZO[B]FURAN Structure

4-AZABENZO[B]FURAN

ETHYL 3-(2-ETHOXY-2-OXOETHOXY)PICOLINATE Structure

ETHYL 3-(2-ETHO...

~%

4-AZABENZO[B]FURAN Structure

4-AZABENZO[B]FURAN

Ethanone, 1-(3-ethoxy-2-pyridinyl)- (9CI) Structure

Ethanone, 1-(3-...

~51%

Ethanone,1-(3-hydroxy-2-pyridinyl)- Structure

Ethanone,1-(3-h...

Ethyl 3-hydroxypicolinate Structure

Ethyl 3-hydroxy...

ethyl 2-bromoacetate Structure

ethyl 2-bromoacetate

~83%

ETHYL 3-(2-ETHOXY-2-OXOETHOXY)PICOLINATE Structure

ETHYL 3-(2-ETHO...

3-Hydroxypicolinic acid Structure

3-Hydroxypicoli...

~%

ETHYL 3-(2-ETHOXY-2-OXOETHOXY)PICOLINATE Structure

ETHYL 3-(2-ETHO...

Synthesis of Functionalized Azomethine Ylides via the Rh (II...

[Padwa, Albert; Dean, Dennis C.; Osterhout, Martin H.; Precedo, Laura; Semones, Mark A. Journal of Organic Chemistry, 1994 , vol. 59, # 18 p. 5347 - 5357]