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Cas Database

535921-10-9

535921-10-9

Identification

  • Product Name:4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

  • CAS Number: 535921-10-9

  • EINECS:

  • Molecular Weight:319.317

  • Molecular Formula: C19H13NO4

  • HS Code:

  • Mol File:535921-10-9.mol

Synonyms:

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Relevant articles and documentsAll total 1 Articles be found

Efficient synthesis of trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives from 4-hydroxycoumarin

Liao, Yuan-Xiu,Kuo, Pei-Yu,Yang, Ding-Yah

, p. 1599 - 1602 (2007/10/03)

Various trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives have been synthesized from 4-hydroxycoumarin with a 30-40% yield over six steps. The key step of the synthesis is a base-promoted intramolecular cyclization of enamines 5, followed by dehydration to generate the fused pyrrole ring.

Process route upstream and downstream products

Process route

(3-benzoyl-2-oxo-2<i>H</i>-chromen-4-ylamino)-acetic acid methyl ester
535921-05-2

(3-benzoyl-2-oxo-2H-chromen-4-ylamino)-acetic acid methyl ester

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
With sodium methylate; In methanol;
4-hydroxy[1]benzopyran-2-one
1076-38-6,92395-12-5

4-hydroxy[1]benzopyran-2-one

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2
2: KCN; Et3N / CH2Cl2 / 48 h / 20 °C
3: diethyl ether
4: Et3N / methanol / 0.5 h / 20 °C
5: MeONa / methanol
With potassium cyanide; sodium methylate; triethylamine; In methanol; diethyl ether; dichloromethane;
3-benzoyl-4-hydroxy-2H-chromen-2-one
19492-11-6

3-benzoyl-4-hydroxy-2H-chromen-2-one

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: diethyl ether
2: Et3N / methanol / 0.5 h / 20 °C
3: MeONa / methanol
With sodium methylate; triethylamine; In methanol; diethyl ether;
2-oxo-2H-chromen-4-yl benzoate
16709-58-3

2-oxo-2H-chromen-4-yl benzoate

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: KCN; Et3N / CH2Cl2 / 48 h / 20 °C
2: diethyl ether
3: Et3N / methanol / 0.5 h / 20 °C
4: MeONa / methanol
With potassium cyanide; sodium methylate; triethylamine; In methanol; diethyl ether; dichloromethane;
4-methoxy-3-benzoylcoumarin
535921-01-8

4-methoxy-3-benzoylcoumarin

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: Et3N / methanol / 0.5 h / 20 °C
2: MeONa / methanol
With sodium methylate; triethylamine; In methanol;
4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

1-benzyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester

1-benzyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
With potassium carbonate; In acetone; at 20 ℃;
4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

1-ethyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester

1-ethyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
With potassium carbonate; In acetone; at 20 ℃;
4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester
535921-10-9

4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

methyl iodide
74-88-4

methyl iodide

1-methyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[<i>a</i>]naphthalene-2-carboxylic acid methyl ester

1-methyl-4-oxo-3-phenyl-1,4-dihydro-5-oxa-1-aza-cyclopenta[a]naphthalene-2-carboxylic acid methyl ester

Conditions
Conditions Yield
With potassium carbonate; In acetone; at 20 ℃; for 8h;

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