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

Ring transformations of heterocycles. Part 1. Transformation of 4??amino?螃?2??1, 2, 4??oxadiazolines into 1, 3, 4??oxadiazoles

MM El??Abadelah, MZ Nazer…

Index: El-Abadelah, M. M.; Nazer, M. Z.; Hussein, A. Q.; Awadallah, A. M.; Rademacher, P.; Woydt, M. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 5 p. 1229 - 1234

Full Text: HTML

Citation Number: 8

Abstract

Abstract 3-Aryl-4-amino-δ 2-1, 2, 4-oxadiazolines 3 and their N-chloroacetyl derivatives 4, upon treatment with chloroacetic anhydride in refluxing toluene, afford 2-chloromethyl-5-aryl- 1, 3, 4-oxadiazoles 5, suggesting the conversion sequence 3→ 4→ 5. The generality of the new ring transformation 4→ 5 is supported similar conversion of other 4-(acylamino)-1, 2, 4- oxadiazolines 8 to 1, 3, 4-oxadiazoles 9.

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-amine Structure

3-(3-nitropheny...

~%

2-(3-Nitrophenyl)-1,3,4-oxadiazole Structure

2-(3-Nitropheny...

2-chloro-N-(3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-yl)acetamide Structure

2-chloro-N-(3-(...

~86%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

ALPHA-CHLORO-3-NITROBENZALDOXIME Structure

ALPHA-CHLORO-3-...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-amine Structure

3-(3-nitropheny...

Chloroacetic anhydride Structure

Chloroacetic an...

~74%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-amine Structure

3-(3-nitropheny...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

2-chloro-N-(5,5-dimethyl-3-(3-nitrophenyl)-1,2,4-oxadiazol-4(5H)-yl)acetamide Structure

2-chloro-N-(5,5...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

2-chloro-N-(3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-yl)acetamide Structure

2-chloro-N-(3-(...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

2-chloro-N-(3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.6]undec-2-en-4-yl)acetamide Structure

2-chloro-N-(3-(...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

2-chloro-N-(8-methyl-3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-yl)acetamide Structure

2-chloro-N-(8-m...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

2-chloro-N-(3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.7]dodec-2-en-4-yl)acetamide Structure

2-chloro-N-(3-(...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

5,5-dimethyl-3-(3-nitrophenyl)-1,2,4-oxadiazol-4(5H)-amine Structure

5,5-dimethyl-3-...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-amine Structure

3-(3-nitropheny...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.6]undec-2-en-4-amine Structure

3-(3-nitropheny...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

8-methyl-3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-amine Structure

8-methyl-3-(3-n...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.7]dodec-2-en-4-amine Structure

3-(3-nitropheny...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

5,5-dimethyl-3-(3-nitrophenyl)-1,2,4-oxadiazol-4(5H)-amine Structure

5,5-dimethyl-3-...

Chloroacetic anhydride Structure

Chloroacetic an...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-amine Structure

3-(3-nitropheny...

Chloroacetic anhydride Structure

Chloroacetic an...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.6]undec-2-en-4-amine Structure

3-(3-nitropheny...

Chloroacetic anhydride Structure

Chloroacetic an...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

8-methyl-3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.5]dec-2-en-4-amine Structure

8-methyl-3-(3-n...

Chloroacetic anhydride Structure

Chloroacetic an...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

3-(3-nitrophenyl)-1-oxa-2,4-diazaspiro[4.7]dodec-2-en-4-amine Structure

3-(3-nitropheny...

Chloroacetic anhydride Structure

Chloroacetic an...

~%

2-CHLOROMETHYL-5-(3-NITRO-PHENYL)-[1,3,4]OXADIAZOLE Structure

2-CHLOROMETHYL-...

N/A Structure

~71%

2-(chloromethyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-(chloromethyl...

3-(4-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-amine Structure

3-(4-nitropheny...

Chloroacetic anhydride Structure

Chloroacetic an...

~75%

2-(chloromethyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-(chloromethyl...

3-(4-nitrophenyl)-1-oxa-2,4-diazaspiro[4.4]non-2-en-4-amine Structure

3-(4-nitropheny...

~%

2-(chloromethyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole Structure

2-(chloromethyl...

Silica Sulfuric Acid: An Efficient and Versatile Acidic Cata...

[Dabiri, Minoo; Salehi, Peyman; Baghbanzadeh, Mostafa; Zolfigol, Mohammad Ali; Bahramnejad, Mahboobeh Synthetic Communications, 2007 , vol. 37, # 7 p. 1201 - 1209]

1, 3, 4-Thiadiazole derivatives. Synthesis, structure elucid...

[Hussein, Ahmad Q.; El-Abadelah, Mustafa M.; Nazer, Musa Z.; Awadallah, Adel M. Heterocycles, 1994 , vol. 38, # 5 p. 981 - 990]