Production Method 1

3290-99-1

829-35-6

Reaction Conditions

1.1 12 h, reflux

Reference

Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues

Hedouin, Jonathan; et al, Organic Letters, 2018, 20(19), 6027-6032

Production Method 2

3290-99-1

829-35-6

Reaction Conditions

1.1 Catalysts: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O) (Al(3+) exchanged) ;  15 min, 55 °C

Reference

Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst

Suresh, Dhanusu; et al, Tetrahedron Letters, 2014, 55(27), 3678-3682

Production Method 3

1957190-76-9

3290-99-1

829-35-6

Reaction Conditions

1.1 Catalysts: Trifluoroacetic acid Solvents: Toluene ;  12 h, 130 °C; 130 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Synthesis of 1,3,4-Oxadiazoles via Annulation of Hydrazides and Benzene-1,3,5-triyl Triformate under Metal-Free Conditions

Yin, Zhiping; et al, Synthesis, 2018, 50(16), 3238-3242

Production Method 4

3290-99-1

829-35-6

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Phosphorus oxychloride Solvents: Toluene ,  Water ;  rt; 30 min, rt; 3 - 4 h, reflux; reflux → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt; cooled

Reference

Synthesis and antimicrobial evaluation of newer 1,3,4-oxadiazole derivatives containing R-phenyl moiety under conventional conditions

Pagare, Ashwini H.; et al, International Journal of TechnoChem Research, 2016, 2(2), 158-164

Production Method 5

28004-70-8

829-35-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  rt; cooled

Reference

Synthesis and antimicrobial evaluation of newer 1,3,4-oxadiazole derivatives containing R-phenyl moiety under conventional conditions

Pagare, Ashwini H.; et al, International Journal of TechnoChem Research, 2016, 2(2), 158-164

Production Method 6

121-98-2

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  8 h, reflux
2.1 Solvents: Ethanol ;  5 h, 140 °C

Reference

Synthesis of 2-aryl-5-(arylsulfonyl)-1,3,4-oxadiazoles as potent antibacterial and antioxidant agents

Boddapati, S. N. Murthy; et al, Turkish Journal of Chemistry, 2022, 46(3), 766-776

Production Method 7

121-98-2

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) ;  2 h, 80 °C
2.1 Catalysts: p-Toluenesulfonic acid Solvents: Triethyl orthoformate ;  overnight, 140 °C

Reference

Room-Temperature Copper-Catalyzed Oxidation of Electron-Deficient Arenes and Heteroarenes Using Air

Liu, Qiang; et al, Angewandte Chemie, 2012, 51(19), 4666-4670

Production Method 8

94-30-4

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  30 h, 100 °C
2.1 Solvents: Triethyl orthoformate ;  4 h, 140 °C

Reference

A Metal-Free Route to 2-Aminooxazoles by Taking Advantage of the Unique Ring Opening of Benzoxazoles and Oxadiazoles with Secondary Amines

Joseph, Jomy; et al, Chemistry - A European Journal, 2011, 17(30), 8294-8298

Production Method 9

100-09-4

829-35-6

Reaction Conditions

1.1 Reagents: Sulfuric acid ;  4 h, reflux
2.1 Reagents: Hydrazine hydrate (1:1) Solvents: Methanol ,  Water ;  4 h, reflux
3.1 Catalysts: p-Toluenesulfonic acid ;  4 h, reflux

Reference

A base-induced ring-opening process of 2-substituted-1,3,4-oxadiazoles for the generation of nitriles at room temperature

Lu, Guo-ping; et al, Journal of Chemical Research, 2014, 38(6), 371-374

Production Method 10

100-09-4

829-35-6

Reaction Conditions

1.1 Catalysts: Sulfuric acid Solvents: Methanol ;  4 h, 80 °C
2.1 Reagents: Hydrazine hydrate (1:1) ;  2 h, 80 °C
3.1 Catalysts: p-Toluenesulfonic acid Solvents: Triethyl orthoformate ;  overnight, 140 °C

Reference

Room-Temperature Copper-Catalyzed Oxidation of Electron-Deficient Arenes and Heteroarenes Using Air

Liu, Qiang; et al, Angewandte Chemie, 2012, 51(19), 4666-4670

Production Method 11

3290-99-1

829-35-6

Reaction Conditions

1.1 Catalysts: Ammonium chloride Solvents: Ethanol ;  30 min, rt → reflux

Reference

Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl

Gnanasekaran, Krishna Kumar; et al, Tetrahedron Letters, 2014, 55(50), 6776-6778

Production Method 12

3290-99-1

829-35-6

Reaction Conditions

1.1 rt → 140 °C; 6 h, 140 °C

Reference

Amination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant

Wertz, Sebastian; et al, Angewandte Chemie, 2011, 50(48), 11511-11515

Production Method 13

3290-99-1

100-06-1

829-35-6

Reaction Conditions

1.1 Reagents: Iodine Solvents: Dimethyl sulfoxide ,  Water ;  rt; 110 °C
1.2 Reagents: Potassium carbonate ;  15 h, 110 °C

Reference

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones

Gao, Qinghe; et al, Organic Letters, 2015, 17(12), 2960-2963

Production Method 14

288-99-3

696-62-8

829-35-6

Reaction Conditions

1.1 Reagents: Zincate(2-), dichlorobis(2,2,6,6-tetramethyl-1-piperidinyl)-, lithium (1:2), (T-… Solvents: Tetrahydrofuran ;  25 °C; 5 min, 25 °C
1.2 Catalysts: Tetrakis(triphenylphosphine)palladium ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] ;  2 h, 50 °C
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases

Schwaerzer, Kuno; et al, Organic Letters, 2020, 22(5), 1899-1902

Production Method 15

3290-99-1

1895-39-2

829-35-6

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Solvents: Acetonitrile ;  1 h, 100 °C

Reference

[4+1] cyclization of benzohydrazide and ClCF2COONa towards 1,3,4-oxadiazoles and 1,3,4-oxadiazoles-d5

Wang, Ya; et al, Chinese Chemical Letters, 2022, 33(3), 1511-1514

Production Method 16

3290-99-1

829-35-6

Reaction Conditions

1.1 Reagents: Lithium perchlorate Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  1.5 h, 100 °C
1.2 Reagents: Water

Reference

Synthesis of N-Sulfonyl Amidines and 1,3,4-Oxadiazoles through Electrochemical Activation of DMF

Mahanty, Kingshuk; et al, Advanced Synthesis & Catalysis, 2023, 365(1), 96-103

Production Method 17

3290-99-1

829-35-6

Reaction Conditions

1.1 Reagents: Potassium persulfate Catalysts: Cuprous iodide ;  1 h, 120 °C

Reference

DMF as Methine Source: Copper-Catalyzed Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles

Wang, Shoucai; et al, Advanced Synthesis & Catalysis, 2019, 361(17), 3986-3990

Production Method 18

3290-99-1

829-35-6

Reaction Conditions

1.1 Reagents: Iodine ,  Oxygen Solvents: Dimethyl sulfoxide ;  6 h, 120 °C
1.2 Reagents: Potassium carbonate ,  Oxygen ;  2 h, 120 °C

Reference

Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond

Fan, Yuxing; et al, Journal of Organic Chemistry, 2016, 81(15), 6820-6825

Production Method 19

3290-99-1

829-35-6

Reaction Conditions

1.1 Reagents: Iodine ,  Oxygen Solvents: Dimethyl sulfoxide ;  6 h, 120 °C
1.2 Reagents: Potassium carbonate ,  Oxygen ;  2 h, 120 °C

Reference

Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond

Fan, Yuxing; et al, Journal of Organic Chemistry, 2016, 81(15), 6820-6825

Production Method 20

100-09-4

829-35-6

Reaction Conditions

1.1 Reagents: Methyl iodide ,  Potassium carbonate Solvents: Dimethylformamide ;  15 min, rt; 10 h, rt
1.2 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  10 h, reflux
1.3 8 h, 140 °C

Reference

Transition metal-free direct C-H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes

Zou, Liang-Hua; et al, Chemical Communications (Cambridge, 2012, 48(92), 11307-11309

Production Method 21

121-98-2

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Methanol ,  Water ;  4 h, reflux
2.1 Catalysts: p-Toluenesulfonic acid ;  4 h, reflux

Reference

A base-induced ring-opening process of 2-substituted-1,3,4-oxadiazoles for the generation of nitriles at room temperature

Lu, Guo-ping; et al, Journal of Chemical Research, 2014, 38(6), 371-374

Production Method 22

628-36-4

829-35-6

Reaction Conditions

1.1 Reagents: Phosphorus pentoxide ;  4 h, 100 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized, cooled
2.1 Reagents: Zincate(2-), dichlorobis(2,2,6,6-tetramethyl-1-piperidinyl)-, lithium (1:2), (T-… Solvents: Tetrahydrofuran ;  25 °C; 5 min, 25 °C
2.2 Catalysts: Tetrakis(triphenylphosphine)palladium ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] ;  2 h, 50 °C
2.3 Reagents: Ammonium chloride Solvents: Water

Reference

Functionalization of 1,3,4-Oxadiazoles and 1,2,4-Triazoles via Selective Zincation or Magnesiation Using 2,2,6,6-Tetramethylpiperidyl Bases

Schwaerzer, Kuno; et al, Organic Letters, 2020, 22(5), 1899-1902

Production Method 23

94-30-4

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) ;  30 min, rt; 8 - 9 h, 60 °C
2.1 Reagents: Potassium hydroxide ,  Phosphorus oxychloride Solvents: Toluene ,  Water ;  rt; 30 min, rt; 3 - 4 h, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt; cooled

Reference

Synthesis and antimicrobial evaluation of newer 1,3,4-oxadiazole derivatives containing R-phenyl moiety under conventional conditions

Pagare, Ashwini H.; et al, International Journal of TechnoChem Research, 2016, 2(2), 158-164

Production Method 24

94-30-4

829-35-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  2 h, 5 °C → reflux
2.1 12 h, 100 - 110 °C

Reference

Synthesis of novel 1-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]piperazine derivatives and evaluation of their in vivo anticonvulsant activity

Harish, Kikkeri P.; et al, European Journal of Medicinal Chemistry, 2013, 65, 276-283

Production Method 25

100-09-4

829-35-6

Reaction Conditions

1.1 Catalysts: Sulfuric acid ;  30 min, rt
2.1 Reagents: Hydrazine hydrate (1:1) ;  30 min, rt; 8 - 9 h, 60 °C
3.1 Reagents: Potassium hydroxide ,  Phosphorus oxychloride Solvents: Toluene ,  Water ;  rt; 30 min, rt; 3 - 4 h, reflux; reflux → rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  rt; cooled

Reference

Synthesis and antimicrobial evaluation of newer 1,3,4-oxadiazole derivatives containing R-phenyl moiety under conventional conditions

Pagare, Ashwini H.; et al, International Journal of TechnoChem Research, 2016, 2(2), 158-164

Production Method 26

100-09-4

829-35-6

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Ethanol ;  5 h, 5 °C → reflux
2.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  2 h, 5 °C → reflux
3.1 12 h, 100 - 110 °C

Reference

Synthesis of novel 1-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]piperazine derivatives and evaluation of their in vivo anticonvulsant activity

Harish, Kikkeri P.; et al, European Journal of Medicinal Chemistry, 2013, 65, 276-283

2-(4-Methoxyphenyl)-1,3,4-oxadiazole Raw materials

• p-Anisic acid
• Ethyl 4-methoxybenzoate
• 1,3,4-Oxadiazole
• TFBen
• 4-Methoxybenzohydrazide
• 4-Iodoanisole
• Sodium chlorodifluoroacetate
• Methyl 4-methoxybenzoate
• 1,2-Diformylhydrazine
• 1-(4-methoxyphenyl)ethan-1-one

2-(4-Methoxyphenyl)-1,3,4-oxadiazole Preparation Products

• 2-(4-Methoxyphenyl)-1,3,4-oxadiazole (829-35-6)

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• 38736-17-3(1,3,4-Oxadiazole,2-(4-methoxyphenyl)-5-(2-naphthalenyl)-)
• 38736-16-2(1,3,4-Oxadiazole,2-(4-methoxyphenyl)-5-(1-naphthalenyl)-)
• 1874-41-5(2-(3-Methoxyphenyl)-5-phenyl-1,3,4-oxadiazole)
• 68047-40-5(2-(3-methoxyphenyl)-5-(2-naphthyl)-1,3,4-oxadiazole)
• 842-79-5(1,3,4-Oxadiazole,2-(4-methoxyphenyl)-5-phenyl-)
• 95903-95-0(1,3,4-Oxadiazole, 2,2'-(oxydi-4,1-phenylene)bis[5-phenyl-)
• 847-39-2(1,3,4-Oxadiazole,2,5-bis(4-methoxyphenyl)-)
• 52596-94-8(2-(4-methoxyphenyl)-5-(4-methylphenyl)-1,3,4-oxadiazole)
• 19748-58-4(2,5-BIS(3-METHOXYPHENYL)-1,3,4-OXADIAZOLE)
• 5378-27-8(4-(1,3,4-Oxadiazol-2-yl)phenol)