PRACTICAL SYNTHESIS OF T-3761, (S)-10-(1-AMINOCYCLOPROPYL)-9-FLUORO-3-METHYL-7-OXO-2,3-DIHYDRO-7H-PYRIDO[1,2,3-DE]-1,4-BENZOXAZINE-6-CARBOXYLIC ACID

被引：0

作者：

TODO, Y

TAKAGI, H

IINO, F

HAYASHI, K

TAKATA, M

KURODA, H

MOMONOI, K

NARITA, H

机构：

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1994年 / 42卷 / 12期

关键词：

FLUOROQUINOLONE; SYNTHESIS; AMINOCYCLOPROPYL SUBSTITUENT; PYRIDOBENZOXAZINE; ANTIBACTERIAL AGENT;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An economical 11-step synthesis of T-3761 (1), a new quinolone antibacterial agent discovered by us, has been developed. Commercially available 2,3,4,5-tetrafluorobenzoic acid (2) has been transformed to 4-(1-acetaminocydopropyl)-2,3,5-trifluorobenzoic acid (10) in 6 steps (68% yield), including cyclopropane-ring formation of the 4-cyanomethylbenzoate intermediate (6) at its side chain. Conversion of 10 to the beta-keto ester 11 and a subsequent 2-step pyridoxazine annulation procedure afforded 13 (80% yield), which, on N,O-deprotection, provided 1 (48% overall yield from 2). The overall reaction sequence can be carried out without chromatographic purification of intermediates.

引用

页码：2629 / 2632

页数：4

共 50 条

[31] 4-Hydroxy-2-Quinolones. 233*. Synthesis and Diuretic Activity of 9-Bromo-7-Hydroxy-5-Oxo-2,3-Dihydro-1H,5H-Pyrido[3,2,1-ij]Quinoline-6-Carboxylic Acid Anilides
I. V. Ukrainets
N. Yu. Golik
I. N. Chernenok
Chemistry of Heterocyclic Compounds, 2013, 49 : 1323 - 1330
[32] ASYMMETRIC-SYNTHESIS AND PROPERTIES OF THE ENANTIOMERS OF THE ANTIBACTERIAL AGENT 7-(3-AMINOPYRROLIDIN-1-YL)-1-(2,4-DIFLUOROPHENYL)-1,4-DIHYDRO-6-FLUORO-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID HYDROCHLORIDE
ROSEN, T
CHU, DTW
LICO, IM
FERNANDES, PB
SHEN, L
BORODKIN, S
PERNET, AG
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (08) : 1586 - 1590
[33] 6-CHLORO-1-ETHYL-1,4-DIHYDRO-4-OXO-7-(4-METHYL-1-PIPERAZINYL)-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, C16H19CLN4O3
DATTA, M
HANNAN, SS
TALUKDAR, AN
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 978 - 980
[34] Practical synthesis of 2-pyridone core:: Ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizinone-3-carboxylate
Li, Q
Sowin, T
Claiborne, A
Lijewski, L
Zhang, XL
Raye, K
Mazdiyasni, H
Arnold, W
Melcher, LM
Wang, WB
Hasvold, L
Fung, A
Chu, DTW
Plattner, JJ
HETEROCYCLES, 1999, 51 (06) : 1345 - +
[35] Synthesis and anticancer activity studies of novel 1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)uracil and (6′-substituted)-7- or 9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-7H- or 9H-purines
Nunez, Maria C.
Pavani, Maria G.
Diaz-Gavilan, Monica
Rodriguez-Serrano, Fernando
Gomez-Vidal, Jose A.
Marchal, Juan A.
Aranega, Antonia
Gallo, Miguel A.
Espinosa, Antonio
Campos, Joaquin M.
TETRAHEDRON, 2006, 62 (50) : 11724 - 11733
[36] An Efficient Synthesis of Ethyl 7-Chloro-6-fluoro-1-methyl-4-oxo-1,4-dihydro-[1, 3]thiazeto[3, 2-a]quinoline-3-carboxylate as Intermediate of the Prulifloxacin Containing Tricyclic Fluoroquinolone
Shu Tao MA
ChineseChemicalLetters, 2006, (06) : 714 - 716
[37] Synthesis and antibacterial activity of 9-cyclopropyl-4-fluoro-6-oxo-6,9-dihydro-[1,2,5]thiadiazolo[3,4-h]quinoline-7-carboxylic acid and its ethyl ester
Al-Qawasmeh, Raed A.
Zahra, Jalal A.
Zani, Franca
Vicini, Paola
Boese, Roland
El-Abadelah, Mustafa M.
ARKIVOC, 2009, : 322 - 336
[38] STRUCTURE OF THE HYDRATE FORM OF 3-METHYL-2-OXO-6,7-DIHYDRO-3H-PYRIMIDO-[5,4-B][1,4]THIAZINE-7-CARBOXYLIC ACID
WEI, CH
SUTTLE, BE
PAL, BC
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 : 116 - 119
[39] Synthesis and Structure of 7-Hydroxy-5-Oxo-2,3-Dihydro-5H-[1,3]Thiazolo[3,2-a]-Pyrimidine-6-Carboxylic Acid Ethyl Ester
I. V. Ukrainets
L. A. Grinevich
T. V. Alekseeva
Pharmaceutical Chemistry Journal, 2017, 51 : 56 - 59
[40] Synthesis and Structure of 7-Hydroxy-5-Oxo-2,3-Dihydro-5H-[1,3]Thiazolo[3,2-a]-Pyrimidine-6-Carboxylic Acid Ethyl Ester
Ukrainets, I. V.
Grinevich, L. A.
Alekseeva, T. V.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2017, 51 (01) : 56 - 59

← 1 2 3 4 5 →