Structures of the racemate and (S)-enantiomer of 7,8-difluoro-3-methyl-2,3-dihydro-4H-[1,4]benzoxazine

被引：13

作者：

Slepukhin, P. A. ^{[1
]}

Gruzdev, D. A. ^{[1
]}

Chulakov, E. N. ^{[1
]}

Levit, G. L. ^{[1
]}

Krasnov, V. P. ^{[1
]}

Charushin, V. N. ^{[1
]}

机构：

[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620990, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2011年 / 60卷 / 05期

基金：

俄罗斯基础研究基金会;

关键词：

X-ray diffraction analysis; enantiomers; racemates; 2,3-dihydro-4H-[1,4]benzoxazines; organofluorine compounds; OPTICALLY-ACTIVE OFLOXACIN; ANTIBACTERIAL ACTIVITIES; KEY INTERMEDIATE; LEVOFLOXACIN; RESOLUTION; CYCLIZATION; REDUCTION;

D O I：

10.1007/s11172-011-0150-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The comparative X-ray diffraction study of racemic and (S)-enantiomer of 7,8-difluoro-3-methyl-2,3-dihydro-4H-[1,4]benzoxazine was carried out. The both forms of benzoxazine are crystallized in the orthorhombic crystal system, the (S)-enantiomer is crystallized in the chiral space group P2(1)2(1)2(1), while the racemate is crystallized in the centrosymmetric Pbca space group. The bond lengths and bond and torsional angles in the both molecules are almost equal. The packing of the racemate is characterized by a closer interaction of polar NHaEuro broken vertical bar O groups.

引用

页码：955 / 960

页数：6

共 17 条

[1] ASYMMETRIC REDUCTION OF 7,8-DIFLUORO-3-METHYL-2H-1,4-BENZOXAZINE - SYNTHESIS OF A KEY INTERMEDIATE OF (S)-(-)-OFLOXACIN (DR-3355) [J].

ATARASHI, S ;

TSURUMI, H ;

FUJIWARA, T ;

HAYAKAWA, I .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) :329-331

[2]

ATARASHI S, 1987, CHEM PHARM BULL, V35, P1896

[3] Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin [J].

Bower, John F. ;

Szeto, Peter ;

Gallagher, Timothy .

ORGANIC LETTERS, 2007, 9 (17) :3283-3286

[4] Dihydrobenzoxazines and tetrahydroquinoxalines by a tandem reduction-reductive amination reaction [J].

Bunce, RA ;

Herron, DM ;

Hale, LY .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 40 (06) :1031-1039

[5]

*CCDC, 2010, CAMBR STRUCT DAT VER

[6] Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazines with (S)-naproxen [J].

Charushin, VN ;

Krasnov, VP ;

Levit, GL ;

Korolyova, MA ;

Kodess, MI ;

Chupakhin, ON ;

Kim, MH ;

Lee, HS ;

Park, YJ ;

Kim, KC .

TETRAHEDRON-ASYMMETRY, 1999, 10 (14) :2691-2702

[7] SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF OPTICALLY-ACTIVE OFLOXACIN [J].

HAYAKAWA, I ;

ATARASHI, S ;

YOKOHAMA, S ;

IMAMURA, M ;

SAKANO, KI ;

FURUKAWA, M .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1986, 29 (01) :163-164

[8]

HAYAKAWA I, 1984, CHEM PHARM BULL, V32, P4907

[9]

Joung MJ, 2002, J HETEROCYCLIC CHEM, V39, P1065

[10] A facile synthesis of (S)-(-)-7,8-difluoro-3,4-dihydro-3-methyl-2H-1,4-benzoxazine by zinc chloride assisted Mitsunobu cyclization reaction [J].

Kang, SB ;

Ahn, EJ ;

Kim, Y ;

Kim, YH .

TETRAHEDRON LETTERS, 1996, 37 (52) :9317-9320

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