Fluoro heterocycles.: A photochemical methodology for the synthesis of 3-amino- and 3-(N-alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles

被引：24

作者：

Buscemi, S ^{[1
]}

Pace, A ^{[1
]}

Vivona, N ^{[1
]}

机构：

[1] Univ Palermo, Dipartimento Chim Organ E Paterno, I-90128 Palermo, Italy

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 41期

关键词：

perfluoroalkanoylamino-furazans; photolysis; perfluoroalkylheterocycles; oxadiazoles;

D O I：

10.1016/S0040-4039(00)01375-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photochemical methodology for the synthesis of perfluoroalkyl-1,2,4-oxadiazoles has been described. 3-Amino- and 3-(N-alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles have been prepared by irradiation of 3-perfluoroalkanoylamino-4-phenyl-1,2,5-oxadiazoles (furazans) at lambda=313 nm in methanol and in the presence of ammonia or primary aliphatic amines. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：7977 / 7981

页数：5

相关论文

共 19 条

[1]

ANGELICO F, 1936, GAZZ CHIM ITAL, V66, P3

[2] SYNTHESIS OF 1,2,4-OXADIAZOLE-DERIVED, 1,3,4-OXADIAZOLE-DERIVED, AND 1,2,4-TRIAZOLE-DERIVED DIPEPTIDOMIMETICS [J].

BORG, S ;

ESTENNEBOUHTOU, G ;

LUTHMAN, K ;

CSOREGH, I ;

HESSELINK, W ;

HACKSELL, U .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3112-3120

[3] FLUORO HETEROCYCLES WITH 5-MEMBERED RINGS [J].

BURGER, K ;

WUCHERPFENNIG, U ;

BRUNNER, E .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 60, 1994, 60 :1-64

[4] Photoinduced single electron transfer on 5-aryl-1,2,4-oxadiazoles: Some mechanistic investigations in the synthesis of quinazolin-4-ones [J].

Buscemi, S ;

Pace, A ;

Vivona, N ;

Caronna, T ;

Galia, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7028-7033

[5] PHOTOINDUCED MOLECULAR-REARRANGEMENTS - SOME INVESTIGATIONS OF THE PHOTOCHEMICAL BEHAVIOR OF 3-(ACYLAMINO)-1,2,5-OXADIAZOLES (FURAZANS) [J].

BUSCEMI, S ;

VIVONA, N ;

CARONNA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4096-4101

[6]

BUSCEMI S, 1995, SYNTHESIS-STUTTGART, P917

[7] Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles [J].

Buscemi, S ;

Vivona, N ;

Caronna, T .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8397-8401

[8] 1,2,4-OXADIAZOLES [J].

CLAPP, LB .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 :65-116

[9] OXADIAZOLES AS ESTER BIOISOSTERIC REPLACEMENTS IN COMPOUNDS RELATED TO DISOXARIL - ANTIRHINOVIRUS ACTIVITY [J].

DIANA, GD ;

VOLKOTS, DL ;

NITZ, TJ ;

BAILEY, TR ;

LONG, MA ;

VESCIO, N ;

ALDOUS, S ;

PEVEAR, DC ;

DUTKO, FJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2421-2436

[10] Synthesis of oxadiazoles on solid support [J].

Hébert, N ;

Hannah, AL ;

Sutton, SC .

TETRAHEDRON LETTERS, 1999, 40 (49) :8547-8550