Use of 2,3-dibromo-1-(phenylsulfonyl)-1-propene as a reagent for the synthesis of annulated furans
Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted and 2,3-fused bicyclic furans in high yield. Formation of the furan ring involves a sequence of addition-elimination, deacetylation, and SN2 d...
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| Published in | Journal of organic chemistry Vol. 55; no. 14; pp. 4241 - 4242 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.07.1990
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-3263 1520-6904 |
| DOI | 10.1021/jo00301a006 |
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| Abstract | Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted and 2,3-fused bicyclic furans in high yield. Formation of the furan ring involves a sequence of addition-elimination, deacetylation, and SN2 displacement reactions. |
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| AbstractList | Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted and 2,3-fused bicyclic furans in high yield. Formation of the furan ring involves a sequence of addition-elimination, deacetylation, and SN2 displacement reactions. |
| Author | Murphree, S. Shaun Padwa, Albert Yeske, Philip E |
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| Keywords | Cycloaddition Base catalysis Sulfone Bicyclic compound Bromine Organic compounds Diketone Oxygen heterocycle |
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| References | COOPER, JA (WOS:A1988N309300028) 1988; 29 TANIS, SP (WOS:A1987H550100015) 1987; 28 HIKINO, H (WOS:A1976BK54500014) 1976; 4 TAYLOR, EC (WOS:A1968A986800039) 1968; 90 ZANI, CL (WOS:A1987L712400008) 1987; 28 HIROTA, H (WOS:A1987K719500056) 1987 GRIECO, PA (WOS:A1975V650000050) 1975; 40 MAGNUS, PD (WOS:A1977DS32600002) 1977; 33 BUCHI, G (WOS:A1969D196500017) 1969; 34 STIRLING CJM (WOS:A1990DM90900006.18) 1964 PADWA, A (WOS:A1988N641100020) 1988; 53 JACOBI PA (WOS:A1990DM90900006.13) 1987; 43 CARTE, B (WOS:A1986D987800025) 1986; 51 JULIA, M (WOS:A1986C396600010) 1986; 42 HAGIWARA, H (WOS:A1984SB50300013) 1984 GLOMBIK, H (WOS:A1983RL55200012) 1983; 116 DEAN, FM (WOS:A1982NJ12100006) 1982; 30 TORI, K (WOS:A1975AZ40500015) 1975 DONNELLY DMX (WOS:A1990DM90900006.7) 1984; 4 DEVON TK (WOS:A1990DM90900006.6) 1972; 2 BOTTEGHI, C (WOS:A1973Q070400017) 1973; 38 STETTER H (WOS:A1990DM90900006.17) 1964; 2 |
| References_xml | – volume: 33 start-page: 2019 year: 1977 ident: WOS:A1977DS32600002 article-title: RECENT DEVELOPMENTS IN SULFONE CHEMISTRY publication-title: TETRAHEDRON – start-page: 4583 year: 1975 ident: WOS:A1975AZ40500015 article-title: C-13 NMR-SPECTRA OF SOME FURANOSESQUITERPENES, MAJOR COMPONENTS OF LINDERA-STRYCHNIFOLIA publication-title: TETRAHEDRON LETTERS – volume: 2 year: 1964 ident: WOS:A1990DM90900006.17 publication-title: NEWER METHODS PREPAR – volume: 40 start-page: 542 year: 1975 ident: WOS:A1975V650000050 article-title: ORGANOSELENIUM CHEMISTRY - GENERAL FURAN SYNTHESIS publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 116 start-page: 3366 year: 1983 ident: WOS:A1983RL55200012 article-title: A VERSATILE SYNTHESIS OF 2,3-DISUBSTITUTED FURANS publication-title: CHEMISCHE BERICHTE-RECUEIL – volume: 28 start-page: 6561 year: 1987 ident: WOS:A1987L712400008 article-title: EFFICIENT DIRECTED ORTHO-METALATION-BASED ROUTE TO CYTO-TOXIC FURANONAPHTHOQUINONE NATURAL-PRODUCTS publication-title: TETRAHEDRON LETTERS – volume: 38 start-page: 2361 year: 1973 ident: WOS:A1973Q070400017 article-title: OPTICALLY-ACTIVE HETEROAROMATIC-COMPOUNDS .6. 3-SUBSTITUTED FURANS AND THIOPHENES FROM ALPHA,BETA-UNSATURATED ALDEHYDES publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 43 start-page: 6561 year: 1987 ident: WOS:A1990DM90900006.13 publication-title: TETRAHEDRON – volume: 42 start-page: 2469 year: 1986 ident: WOS:A1986C396600010 article-title: SYNTHESES WITH SULFONE AID .37. SYNTHESIS OF THE 3 PHEROMONES WITH A DOUBLE BOND-Z - Z,8-DDA - Z,9-DDA - Z,9-TDA publication-title: TETRAHEDRON – volume: 53 start-page: 2232 year: 1988 ident: WOS:A1988N641100020 article-title: SITE SELECTIVITY IN THE REACTIONS OF VARIOUS 1,3-DIPOLES WITH (PHENYLSULFONYL)-1,2-PROPADIENE publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 28 start-page: 2495 year: 1987 ident: WOS:A1987H550100015 article-title: FURANS IN SYNTHESIS .7. A FORMAL TOTAL SYNTHESIS OF (+/-)-PERHYDROHISTRIONICOTOXIN publication-title: TETRAHEDRON LETTERS – start-page: 2079 year: 1987 ident: WOS:A1987K719500056 article-title: TOTAL SYNTHESIS OF (+/-)-FURODYSIN AND (+/-)-FURODYSININ publication-title: CHEMISTRY LETTERS – volume: 2 year: 1972 ident: WOS:A1990DM90900006.6 publication-title: HDB NATURALLY OCCURR – volume: 51 start-page: 3528 year: 1986 ident: WOS:A1986D987800025 article-title: METABOLITES OF THE NUDIBRANCH CHROMODORIS-FUNEREA AND THE SINGLET OXYGEN OXIDATION-PRODUCTS OF FURODYSIN AND FURODYSININ publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 4 year: 1984 ident: WOS:A1990DM90900006.7 publication-title: COMPREHENSIVE HETE 3 – volume: 34 start-page: 857 year: 1969 ident: WOS:A1969D196500017 article-title: SYNTHESIS OF BILOBANONE publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 90 start-page: 2421 year: 1968 ident: WOS:A1968A986800039 article-title: THALLIUM IN ORGANIC SYNTHESIS .I. ALKYLATION AND ACYLATION OF BETA-DICARBONYL COMPOUNDS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 4 start-page: 817 year: 1976 ident: WOS:A1976BK54500014 article-title: FURANOSESQUITERPENOIDS publication-title: HETEROCYCLES – start-page: 5856 year: 1964 ident: WOS:A1990DM90900006.18 publication-title: J CHEM SOC – volume: 30 start-page: 167 year: 1982 ident: WOS:A1982NJ12100006 article-title: RECENT ADVANCES IN FURAN CHEMISTRY .1. publication-title: ADVANCES IN HETEROCYCLIC CHEMISTRY – start-page: 91 year: 1984 ident: WOS:A1984SB50300013 article-title: NEW ROUTE FOR SYNTHESIS OF FURAN-DERIVATIVES FROM PROTECTED ALPHA-KETOLS AND KETONES - A TOTAL SYNTHESIS OF FUROVENTALENE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – volume: 29 start-page: 2107 year: 1988 ident: WOS:A1988N309300028 article-title: FURANODECALIN SYNTHESIS USING INTRAMOLECULAR DIELS-ALDER REACTIONS OF VINYLFURANS publication-title: TETRAHEDRON LETTERS |
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| Snippet | Treatment of 2,3-dibromo-1-(phenyl-sulfonyl)-1-propene with various .beta.-dicarbonyl compounds in the presence of sodium methoxide affords 2,4-disubstituted... |
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| SubjectTerms | Chemistry Chemistry, Organic Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Physical Sciences Preparations and properties Science & Technology |
| Title | Use of 2,3-dibromo-1-(phenylsulfonyl)-1-propene as a reagent for the synthesis of annulated furans |
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