A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents
Publication
, Journal Article
Rane, DF; Pike, RE; Puar, MS; Wright, JJ; Mcphail, AT
Published in: Tetrahedron
January 1, 1988
Ring contraction of cis-3-bromo-7-chloro-3,4-dihydro-2H-1-benzothiopyran-4-ol 4 in the presence of imidazole results in formation of cis-6-chloro-2,3-dihydro-2-(1H-imidazol-1-ylmethyl) benzo[b]thiophene-3-ol 8 as the major product. The structure of 8 was defined unequivocally by X-ray analysis of a solvated (ethyl acetate) and an unsolvated crystal form. Alkylation of 8 with 3-(bromomethyl)-2-chlorothiophene gave cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzor[b] thien-2-yl]methyl]lH-imidazole 9, a representative of a new class of azole antifungal agents. © 1988.
Duke Scholars
Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
January 1, 1988
Volume
44
Issue
9
Start / End Page
2397 / 2402
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Rane, D. F., Pike, R. E., Puar, M. S., Wright, J. J., & Mcphail, A. T. (1988). A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents. Tetrahedron, 44(9), 2397–2402. https://doi.org/10.1016/S0040-4020(01)81691-4
Rane, D. F., R. E. Pike, M. S. Puar, J. J. Wright, and A. T. Mcphail. “A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents.” Tetrahedron 44, no. 9 (January 1, 1988): 2397–2402. https://doi.org/10.1016/S0040-4020(01)81691-4.
Rane DF, Pike RE, Puar MS, Wright JJ, Mcphail AT. A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents. Tetrahedron. 1988 Jan 1;44(9):2397–402.
Rane, D. F., et al. “A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents.” Tetrahedron, vol. 44, no. 9, Jan. 1988, pp. 2397–402. Scopus, doi:10.1016/S0040-4020(01)81691-4.
Rane DF, Pike RE, Puar MS, Wright JJ, Mcphail AT. A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents. Tetrahedron. 1988 Jan 1;44(9):2397–2402.
Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
January 1, 1988
Volume
44
Issue
9
Start / End Page
2397 / 2402
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry