Synthesis of α-(heteroarylthio)-α,α-difluoroacetophenone derivatives via the SRN1 methodology

被引：21

作者：

Burkholder, C

Dolbier, WR

Médebielle, M

Ait-Mohand, S

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

[2] Univ Paris 07, CNRS, UMR 7591, Lab Electrochim Mol, F-75251 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(01)00513-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New alpha-(heteroarylthio)-alpha,alpha -difluoroacetophenone Ar-1-COCF2S-Ar-2 derivatives 8-15 were synthesized in moderate to good yields via the S(RN)1 methodology, from the reaction of a series of chlorodifuloromethylated ketones 1-4 with aromatic and heterocyclic thiols 5-7. The corresponding Ar-1-CHOHCF2S-Ar-2 16-23 were also prepared in moderate yields, using sodium borohydride in absolute ethanol. The compounds may find some biological applications as potent anti-HIV-l as well as useful synthons for agrochemicals. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：3459 / 3462

页数：4

相关论文

共 13 条

[1] OXIDATIVE FLUORINATION OF SULFIDES IN PRESENCE OF ET3N.3HF [J].

BRIGAUD, T ;

LAURENT, E .

TETRAHEDRON LETTERS, 1990, 31 (16) :2287-2290

[2] Tetrakis(dimethylamino)ethylene (TDAE) as a useful reductant of some chlorodifluoromethylated ketones.: A new approach for the synthesis of α,α-difluoroketone derivatives. [J].

Burkholder, C ;

Dolbier, WR ;

Medebielle, M ;

Ndedi, A .

TETRAHEDRON LETTERS, 1998, 39 (48) :8853-8856

[3] The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group -: The SRN1 reactions of 2-(bromodifluoromethyl)benzoxazole with the anions derived from heterocyclic thiols and phenolic compounds [J].

Burkholder, CR ;

Dolbier, WR ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :369-376

[4] New antifungal 1,2,4-triazoles with difluoro(substituted sulfonyl)methyl moiety [J].

Eto, H ;

Kaneko, Y ;

Takeda, S ;

Tokizawa, M ;

Sato, S ;

Yoshida, K ;

Namiki, S ;

Ogawa, M ;

Maebashi, K ;

Ishida, K ;

Matsumoto, M ;

Asaoka, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (02) :173-182

[5] Fluorination of orthothioesters through oxidative desulfurization-fluorination [J].

Furuta, S ;

Kuroboshi, M ;

Hiyama, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (08) :1939-1951

[6] Electrochemically induced free-radical tandem cyclisation of chlorodifluoromethylated ketones Application to the synthesis of gem-difluorinated heterocycles [J].

Hapiot, P ;

Médebielle, M .

JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) :285-300

[7] ALPHA-EFFECT IN ALPHA-CHLOROFLUORO KETONES [J].

KRESPAN, CG .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :637-640

[8]

Pedersen OS, 2000, SYNTHESIS-STUTTGART, P479

[9]

Rossi R.A., 1990, Advances in Free Radical Chemistry, P193

[10] MECHANISMS AND REACTIVITY IN ELECTRON-TRANSFER-INDUCED AROMATIC NUCLEOPHILIC-SUBSTITUTION - RECENT ADVANCES [J].

SAVEANT, JM .

TETRAHEDRON, 1994, 50 (34) :10117-10165