" BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA)
The synthetic route in this work is based on the classical Friedel-Crafts strategy, and began with 1,4-dimethoxybenzene (I), followed by alkylation and selective demethylation of 2-methoxy function in 0x0-acid (3). The orthoformylation to synthesize aldehyde (6) was based on the Reimer-Tieman reacti...
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| Format: | Article |
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| Language: | English |
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University of Tehran
1996-03-01
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| Series: | Journal of Sciences, Islamic Republic of Iran |
| Online Access: | https://jsciences.ut.ac.ir/article_31107_d43542202cee3071e58a04251bcf5f74.pdf |
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| description | The synthetic route in this work is based on the classical Friedel-Crafts strategy,
and began with 1,4-dimethoxybenzene (I), followed by alkylation and selective
demethylation of 2-methoxy function in 0x0-acid (3). The orthoformylation to
synthesize aldehyde (6) was based on the Reimer-Tieman reaction. Chain extension
of this aldehyde required methylation of the hydroxyl group and condensation with
pyruvic acid which afforded acid (8) in 85% yield. Two steps reduction process of this
acid led to diacid (1 1) in good yield. A direct "biscylisation" of (1 1) afforded diketone
(12) as the main product. This compound was converted to (1,8-DHA), 15, via an
aromatization process |
| format | Article |
| id | doaj-art-e02f3f4a4cfc48b49e8f6cd29b9016a1 |
| institution | DOAJ |
| issn | 1016-1104 2345-6914 |
| language | English |
| publishDate | 1996-03-01 |
| publisher | University of Tehran |
| record_format | Article |
| series | Journal of Sciences, Islamic Republic of Iran |
| spelling | doaj-art-e02f3f4a4cfc48b49e8f6cd29b9016a12025-08-20T03:08:48ZengUniversity of TehranJournal of Sciences, Islamic Republic of Iran1016-11042345-69141996-03-017131107" BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA)The synthetic route in this work is based on the classical Friedel-Crafts strategy, and began with 1,4-dimethoxybenzene (I), followed by alkylation and selective demethylation of 2-methoxy function in 0x0-acid (3). The orthoformylation to synthesize aldehyde (6) was based on the Reimer-Tieman reaction. Chain extension of this aldehyde required methylation of the hydroxyl group and condensation with pyruvic acid which afforded acid (8) in 85% yield. Two steps reduction process of this acid led to diacid (1 1) in good yield. A direct "biscylisation" of (1 1) afforded diketone (12) as the main product. This compound was converted to (1,8-DHA), 15, via an aromatization processhttps://jsciences.ut.ac.ir/article_31107_d43542202cee3071e58a04251bcf5f74.pdf |
| spellingShingle | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) Journal of Sciences, Islamic Republic of Iran |
| title | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) |
| title_full | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) |
| title_fullStr | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) |
| title_full_unstemmed | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) |
| title_short | " BISCYCLISATION" SYNTHESIS OF 1,8-DIHYDROXY-9, 1 0- ANTHRAQUINONE (1,8-DHA) |
| title_sort | biscyclisation synthesis of 1 8 dihydroxy 9 1 0 anthraquinone 1 8 dha |
| url | https://jsciences.ut.ac.ir/article_31107_d43542202cee3071e58a04251bcf5f74.pdf |