Stereoselective Methodology for the Synthesis of an Antifungal Allylamine: Terbinafine

被引：2

作者：

Gupta, Bhavna ^{[1
]}

Babu, B. Ravindra ^{[1
]}

Gyanda, Kapil ^{[1
]}

Panda, Siva S. ^{[1
]}

Jain, Subhash C. ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

LETTERS IN ORGANIC CHEMISTRY | 2014年 / 11卷 / 02期

关键词：

Terbinafine; alkylation; stereoselective synthesis; selective reduction; antifungal drug; DERIVATIVES; EFFICIENT; NAFTIFINE; VINYL;

D O I：

10.2174/15701786113106660078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of an antifungal drug, Terbinafine, bearing (E)-tert-butylenyne structural element as the side chain is achieved by coupling N-methyl-1-napthalene methanamine with 1-bromo-6,6-dimethyl-2E-hepten-4-yne in good yield. The new methodology avoids the use of toxic starting materials like acrolein and phosphorous pentachloride that were used in earlier reports. The structure was confirmed by IR, NMR, MS, and elemental analysis.

引用

下载

页码：141 / 144

页数：4

共 50 条

[21] TERBINAFINE - AN ORAL AND TOPICAL ANTIFUNGAL AGENT
SHEAR, NH
VILLARS, VV
MARSOLAIS, C
CLINICS IN DERMATOLOGY, 1991, 9 (04) : 487 - 495
[22] Systemic antifungal treatment of children with terbinafine
Bruckbauer, HR
Hofmann, H
DERMATOLOGY, 1997, 195 (02) : 134 - 136
[23] Oral terbinafine: A new antifungal agent
AbdelRahman, SM
Nahata, MC
ANNALS OF PHARMACOTHERAPY, 1997, 31 (04) : 445 - 456
[24] Improved methodology for stereoselective synthesis in flow reactors
Wiles, C
Watts, P
Haswell, SJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3190 - U3190
[25] A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin
Yoda, H.
Yamazaki, H.
Takabe, K.
Tetrahedron: Asymmetry, 7 (02):
[26] A novel stereoselective synthesis of enantiomerically pure antifungal agent, (+)-preussin
Yoda, H
Yamazaki, H
Takabe, K
TETRAHEDRON-ASYMMETRY, 1996, 7 (02) : 373 - 374
[27] Terbinafine, a unique oral antifungal: current perceptions
Jain, S
Sehgal, VN
INTERNATIONAL JOURNAL OF DERMATOLOGY, 2000, 39 (06) : 412 - 423
[28] TERBINAFINE: NOVEL FORMULATIONS THAT POTENTIATE ANTIFUNGAL ACTIVITIES
Ma, Y.
Chen, X.
Guan, S.
DRUGS OF TODAY, 2015, 51 (03) : 197 - 208
[29] Synthesis of allylamine in ethanol
唐炳涛
张淑芬
杨锦宗
化工学报, 2005, (10) : 1897 - 1900
[30] Antifungal cotton fabric via molecular encapsulation of terbinafine
Erkan, Gökhan, 1600, Editura Academiei Romane (48): : 7 - 8

← 1 2 3 4 5 →