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25475-67-6 Usage

General Description

ISOQUINOLIN-3-AMINE is a chemical compound that is part of the isoquinoline family, which consists of a group of compounds known for their wide range of biological activities. It is an aromatic compound that features a benzene ring fused to a pyridine ring. As an amine, it consists of a nitrogen atom attached to two hydrogen atoms. ISOQUINOLIN-3-AMINE is primarily used in the chemical industry for synthesizing other compounds and it can be transformed into many different kinds of heterocyclic compounds with a wide range of potential uses, including medicinal use for their antibacterial, antifungal, anti-inflammatory, and anti-tumor properties. It's important to handle this compound with care, as it can be harmful if exposed to the skin or eyes, and could be even more dangerous if inhaled or ingested.

Check Digit Verification of cas no

The CAS Registry Mumber 25475-67-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,4,7 and 5 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 25475-67:
(7*2)+(6*5)+(5*4)+(4*7)+(3*5)+(2*6)+(1*7)=126
126 % 10 = 6
So 25475-67-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H8N2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-6H,(H2,10,11)

25475-67-6 Well-known Company Product Price

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  • Aldrich

  • (730513)  3-Aminoisoquinoline  97%

  • 25475-67-6

  • 730513-1G

  • 981.63CNY

  • Detail
  • Aldrich

  • (ANV00025)  3-Aminoisoquinoline  

  • 25475-67-6

  • ANV00025-1G

  • 1,930.50CNY

  • Detail

25475-67-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name ISOQUINOLIN-3-AMINE

1.2 Other means of identification

Product number -
Other names IFLAB-BB F2108-0097

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:25475-67-6 SDS

25475-67-6Synthetic route

tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate

tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Stage #1: tert-butyl 2-(2-(1,3-dioxolan-2-yl)phenyl)-2-cyanoacetate In ethanol; water at 90℃; for 18h; Sealed tube;
Stage #2: With ammonium chloride In ethanol; water at 90℃; for 3h;
86%
2-(2-formylphenyl)acetonitrile
135737-14-3

2-(2-formylphenyl)acetonitrile

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With ammonia; trifluoroacetic acid In methanol for 4h; Heating;69%
Phenylalanine
150-30-1

Phenylalanine

3-amino-4-bromoisoquinoline
10321-49-0

3-amino-4-bromoisoquinoline

A

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

B

C18H17N3O

C18H17N3O

C

2-benzylpyrazino[2,3-c]isoquinolin-3-ol

2-benzylpyrazino[2,3-c]isoquinolin-3-ol

Conditions
ConditionsYield
With copper(I) oxide; potassium phosphate In dimethyl sulfoxide at 90℃; for 40h; Inert atmosphere;A n/a
B 0.47 g
C 18%
3-chloroisoquinoline
19493-45-9

3-chloroisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With ammonium hydroxide; copper(II) sulfate at 140℃;
3-bromoisoquinoline
34784-02-6

3-bromoisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With ammonium hydroxide; copper(II) sulfate at 140℃;
isoquinoline-3(S)-carboxamide
50458-77-0

isoquinoline-3(S)-carboxamide

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With potassium hydroxide; bromine
With potassium hydroxide; bromine Hofmann degradation; Cooling;
3-amino-4-chloroisoquinoline
66729-00-8

3-amino-4-chloroisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With methanol; sodium methylate at 200℃;
isoquinoline-3-carboxylic acid
6624-49-3

isoquinoline-3-carboxylic acid

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; diazomethane; diethyl ether / Behandeln des Reaktionsprodukts in Methanol mit NH3
2: bromine; aqueous KOH
View Scheme
4-isoquinolinol
3336-49-0

4-isoquinolinol

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid; potassium nitrate
2: phosphoryl chloride
3: palladium/charcoal; ethanol / Hydrogenation
4: sodium methylate; methanol / 200 °C
View Scheme
4-chloro-3-nitroisoquinoline
101860-70-2

4-chloro-3-nitroisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium/charcoal; ethanol / Hydrogenation
2: sodium methylate; methanol / 200 °C
View Scheme
3-nitro-isoquinolin-4-ol
36718-46-4

3-nitro-isoquinolin-4-ol

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphoryl chloride
2: palladium/charcoal; ethanol / Hydrogenation
3: sodium methylate; methanol / 200 °C
View Scheme
isoquinoline-1,3-diol
86-94-2

isoquinoline-1,3-diol

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphorus (III)-bromide
2: acetic acid; aqueous hydriodic acid; red phosphorus
3: CuSO4; aqueous NH3 / 140 °C
View Scheme
1,3-dibromoisoquinoline
53987-60-3

1,3-dibromoisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; aqueous hydriodic acid; red phosphorus
2: CuSO4; aqueous NH3 / 140 °C
View Scheme
3-amino-1-bromoisoquinoline
13130-79-5

3-amino-1-bromoisoquinoline

isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

2-isothiocyanato-1,4-dimethoxybenzene
40532-06-7

2-isothiocyanato-1,4-dimethoxybenzene

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2,5-dimethoxyaniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2,5-dimethoxyaniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 1h;96%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

N-(2-nitrophenyl)isoquinolin-3-amine
1370708-46-5

N-(2-nitrophenyl)isoquinolin-3-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;94%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

1,1'-Thiocarbonyldi-2(1H)-pyridone
102368-13-8

1,1'-Thiocarbonyldi-2(1H)-pyridone

3-isothiocyanatoisoquinoline
769960-94-3

3-isothiocyanatoisoquinoline

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;93%
In dichloromethane at 20℃; for 2h;93%
In dichloromethane at 20℃; for 18h;85%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)aniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)aniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;93%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

acetophenone
98-86-2

acetophenone

2-Phenyl-imidazo<2,1-a>isochinolin
70845-68-0

2-Phenyl-imidazo<2,1-a>isochinolin

Conditions
ConditionsYield
With indium(III) triflate; copper(l) iodide; oxygen In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 30h; Schlenk technique;92%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

1-isothiocyanato-4-methylbenzene
622-59-3

1-isothiocyanato-4-methylbenzene

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-methylaniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-methylaniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 1h;92%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N'-hydroxy-N-(isoquinolin-3-yl)formimidamide

N'-hydroxy-N-(isoquinolin-3-yl)formimidamide

Conditions
ConditionsYield
Stage #1: isoquinolin-3-amine; N,N-dimethyl-formamide dimethyl acetal In isopropyl alcohol at 80℃; for 3h; Inert atmosphere;
Stage #2: With hydroxylamine hydrochloride In isopropyl alcohol at 50℃; for 12h; Inert atmosphere;
92%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

N-(3-chlorophenyl)isoquinolin-3-amine
1370708-39-6

N-(3-chlorophenyl)isoquinolin-3-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;91%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

4-isopropylphenyl isothiocyanate
89007-45-4

4-isopropylphenyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-isopropylaniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-isopropylaniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;91%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

4-Chlorophenyl isothiocyanate
2131-55-7

4-Chlorophenyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-chloroaniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-chloroaniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;89%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

3,4-isoquinolinedione 4-oxime
83939-28-0

3,4-isoquinolinedione 4-oxime

Conditions
ConditionsYield
With sodium nitrite In sulfuric acid 1.) 5-10 deg C, 45 min; 2.) 3-7 deg C, 2.5 h;88%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

bromobenzene
108-86-1

bromobenzene

N-phenylisoquinolin-3-amine

N-phenylisoquinolin-3-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 46h; Buchwald-Hartwig reaction; Inert atmosphere; Reflux;87%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene for 5h; Buchwald-Hartwig Coupling; Inert atmosphere;87%
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 110℃; for 5h; Buchwald-Hartwig arylation; Inert atmosphere;85%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-nitroaniline

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-4-nitroaniline

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;87%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

3-(isoquinolin-3-ylamino)cyclohex-2-en-1-one

3-(isoquinolin-3-ylamino)cyclohex-2-en-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; toluene for 4h; Dean-Stark; Reflux; Inert atmosphere;87%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

O-tosylhydroxylamine
52913-14-1

O-tosylhydroxylamine

2,3-diamino-isoquinolinium 4-methylbenzenesulfonate
75949-14-3

2,3-diamino-isoquinolinium 4-methylbenzenesulfonate

Conditions
ConditionsYield
In dichloromethane at 25℃; for 1h;85%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

para-bromotoluene
106-38-7

para-bromotoluene

N-p-tolylisoquinolin-3-amine
1373873-57-4

N-p-tolylisoquinolin-3-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); johnphos; sodium t-butanolate In toluene at 110℃; for 5h; Buchwald-Hartwig arylation; Inert atmosphere;85%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

ethyl 3-bromobenzoate
24398-88-7

ethyl 3-bromobenzoate

ethyl 3-(isoquinolin-3-ylamino)benzoate
1370708-53-4

ethyl 3-(isoquinolin-3-ylamino)benzoate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 6h; Buchwald-Hartwig Coupling; Inert atmosphere;84%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

2-(isoquinolin-3-ylamino)benzaldehyde
1370708-55-6

2-(isoquinolin-3-ylamino)benzaldehyde

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 2h; Buchwald-Hartwig Coupling; Inert atmosphere;84%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

methyl iodide
74-88-4

methyl iodide

3-(N,N-dimethylamino)isoquinoline

3-(N,N-dimethylamino)isoquinoline

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere;84%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

3-amino-4-chloroisoquinoline
66729-00-8

3-amino-4-chloroisoquinoline

Conditions
ConditionsYield
With N-chloro-succinimide In methanol at 20℃; for 3h;84%
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction;66%
With 1,3-dichloro-5,5-dimethylhydantoin; Isopropyl acetate at -10℃; for 16h; Reagent/catalyst; Temperature;20.52 g
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

phenyl chloroformate
1885-14-9

phenyl chloroformate

isoquinolin-3-ylcarbamic acid phenyl ester

isoquinolin-3-ylcarbamic acid phenyl ester

Conditions
ConditionsYield
With pyridine In acetonitrile at 23℃; for 1h;83%
With pyridine In acetonitrile at 20℃; for 1h;83%
at 0 - 20℃;
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

ethyl 4-(isoquinolin-3-ylamino)benzoate
1370708-54-5

ethyl 4-(isoquinolin-3-ylamino)benzoate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane for 6h; Buchwald-Hartwig Coupling; Inert atmosphere;83%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

Ethyl isothiocyanate
542-85-8

Ethyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)ethanamine

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)ethanamine

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 3h;83%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)

(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(isoquinolin-3-ylamino)gold
1522372-36-6

(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(isoquinolin-3-ylamino)gold

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 20h;82%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

cyclopropyl isothiocyanate
56601-42-4

cyclopropyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)cyclopropanamine

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)cyclopropanamine

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;82%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

tert-butyl isothiocyanate
590-42-1

tert-butyl isothiocyanate

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2-methylpropan-2-amine

N-(3H-[1,2,4]thiadiazolo[4,3-b]isoquinolin-3-ylidene)-2-methylpropan-2-amine

Conditions
ConditionsYield
With montmorillonite K10 Clay In acetonitrile at 20℃; for 2h;82%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

1-(2-ethylphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

1-(2-ethylphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

1-(2-ethylphenyl)-N-(isoquinolin-3-yl)-5-methyl-1H-pyrazole-4-carboxamide

1-(2-ethylphenyl)-N-(isoquinolin-3-yl)-5-methyl-1H-pyrazole-4-carboxamide

Conditions
ConditionsYield
With chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 80℃;82%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

(3E)-4-(4-chlorophenyl)-3-buten-2-one
30626-03-0

(3E)-4-(4-chlorophenyl)-3-buten-2-one

(E)-2-(4-chlorostyryl)imidazo[2,1-a]isoquinoline
1505454-53-4

(E)-2-(4-chlorostyryl)imidazo[2,1-a]isoquinoline

Conditions
ConditionsYield
With indium(III) triflate; copper(l) iodide; oxygen In 1-methyl-pyrrolidin-2-one at 100℃; under 760.051 Torr; for 30h; Schlenk technique;81%
isoquinolin-3-amine
25475-67-6

isoquinolin-3-amine

3-amino-4-bromoisoquinoline
10321-49-0

3-amino-4-bromoisoquinoline

Conditions
ConditionsYield
With N-Bromosuccinimide; ammonium acetate In acetonitrile at 20℃; for 0.0833333h; regioselective reaction;80%
With N-Bromosuccinimide In ethanol; dichloromethane at 5 - 20℃;75%
With N-Bromosuccinimide In ethanol; dichloromethane at 5 - 20℃; for 2.33h;75%

25475-67-6Relevant articles and documents

On Pyridopyrazinol Chemistry: Synthesis of Chemiluminescent Substances

Gagnot, Glwadys,Legrand, Pierre,Tadros, Amira,Ezzahra Hibti, Fatima,Quatela, Alessia,Janin, Yves L.

, p. 2477 - 2484 (2021)

Our work on new chemiluminescent substances related to the marine luciferin coelenterazine (λ max= 465 nm) led us to attempt the synthesis of four nitrogen-rich pyridopyrazine-bearing analogues. Accordingly, the preparation of the corresponding benzyl-bearing pyridopyrazinols is studied. By varying the conditions for the condensation of phenylpyruvic acid with 1,2-diaminopyridine or 3,4-diaminopyridine, all the possible pyridopyrazin-2-ol regioisomers are isolated and properly characterized, including by means of crystallographic studies. The ensuing syntheses of the halogenated pyridopyrazines are fraught with difficulties ranging from extensive decomposition to an unexpected ring contraction. In one instance, the inherently reductive mixture of phosphorus oxychloride and phosphorus trichloride provides 2-benzyl-3-chloropyrido[2,3- b ]pyrazine. This precursor is then transformed into the target O -acetylated luciferin (6,8-dibenzylimidazo[1,2- a ]pyrido[3,2- e ]pyrazin-9-yl acetate). The 'benzo' derivative of this analogue (i.e., 2,12-dibenzylimidazo[1′,2′:1,6]pyrazino[2,3- c ]isoquinolin-3-yl acetate) is also prepared and the chemiluminescence emission spectra of these compounds are determined in a phosphate buffer (λ max= 546 and 462 nm).

-

Sanders et al.

, p. 4717 (1972)

-

New fluorescent isoquinoline derivatives

Balog, József,Riedl, Zsuzsanna,Hajós, Gy?rgy,Miskolczy, Zsombor,Biczók, László

body text, p. 5264 - 5266 (2011/10/19)

Various structural modifications of 3-amino and 3-hydroxyisoquinolines have been carried out to provide new fluorescent derivatives. The transformations involved nucleophilic substitution of a bromine atom or a triflate moiety at positions 1 and 3, respectively, as well as the condensation reaction of a 3-amino group with triethyl orthoformate and subsequent transformation with amines to give amidines. The new compounds have been studied by fluorescence spectroscopy.

A general approach to 3-aminoisoquinoline, its N-mono and N,N-disubstituted derivatives

Zdrojewski,Jonczyk

, p. 12439 - 12444 (2007/10/02)

Condensation of 2-cyanomethyl benzaldehydes 1 with 2 (ammonia, primary or secondary amines) carried out in the presence of a catalytic amount of trifluoroacetic acid, afforded 3-aminoisoquinolines 3. In the case of primary amines azomethines 4 were formed at first; they dissociated and subsequently yielded 3 in a rather slow process.

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