Abstract
The 7-benzyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepin-4-one (11) has been synthesized from the N-benzyl-N-(2-thenyl)-β-alanine (10) by a tin(IV) chloride-catalysed Friedel-Crafts cyclization. In addition, N-benzyl- and N-(p-tolylsulphonyl)-N-(3-thenyl)-β-alanine (16a) and (16b) cyclized more effectively to give 5-benzyl- and 5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H- thieno[3,2-c]azepin-8-one (17a) and (17b), respectively. Attempts to remove the p-tolylsulphonyl group from compound (17b) was achieved by use of polyphosphoric acid (PPA) and afforded the 4,5,6,7-tetrahydro-8H-thieno[3,2-c]azepin-8-one (19). In contrast, 7-bromo-5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H-thieno-[3, 2-c]azepin-8-one (20) gave the novel heterocyclic system, 6,7-dihydroazirino[1, 2-a]-thieno[2,3-d]pyridin-8-one (22) under similar conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 729-732 |
| Number of pages | 4 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Publication status | Published - 1986 |
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ASJC Scopus subject areas
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Synthesis of thieno[2,3-c]- and thieno[3,2-c]-azepinones. / Satake, Kyosuke; Itoh, Kenji; Miyoshi, Yoshiko; Kimura, Masaru; Morosawa, Shiro.
In: Journal of the Chemical Society, Perkin Transactions 1, 1986, p. 729-732.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of thieno[2,3-c]- and thieno[3,2-c]-azepinones
AU - Satake, Kyosuke
AU - Itoh, Kenji
AU - Miyoshi, Yoshiko
AU - Kimura, Masaru
AU - Morosawa, Shiro
PY - 1986
Y1 - 1986
N2 - The 7-benzyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepin-4-one (11) has been synthesized from the N-benzyl-N-(2-thenyl)-β-alanine (10) by a tin(IV) chloride-catalysed Friedel-Crafts cyclization. In addition, N-benzyl- and N-(p-tolylsulphonyl)-N-(3-thenyl)-β-alanine (16a) and (16b) cyclized more effectively to give 5-benzyl- and 5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H- thieno[3,2-c]azepin-8-one (17a) and (17b), respectively. Attempts to remove the p-tolylsulphonyl group from compound (17b) was achieved by use of polyphosphoric acid (PPA) and afforded the 4,5,6,7-tetrahydro-8H-thieno[3,2-c]azepin-8-one (19). In contrast, 7-bromo-5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H-thieno-[3, 2-c]azepin-8-one (20) gave the novel heterocyclic system, 6,7-dihydroazirino[1, 2-a]-thieno[2,3-d]pyridin-8-one (22) under similar conditions.
AB - The 7-benzyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepin-4-one (11) has been synthesized from the N-benzyl-N-(2-thenyl)-β-alanine (10) by a tin(IV) chloride-catalysed Friedel-Crafts cyclization. In addition, N-benzyl- and N-(p-tolylsulphonyl)-N-(3-thenyl)-β-alanine (16a) and (16b) cyclized more effectively to give 5-benzyl- and 5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H- thieno[3,2-c]azepin-8-one (17a) and (17b), respectively. Attempts to remove the p-tolylsulphonyl group from compound (17b) was achieved by use of polyphosphoric acid (PPA) and afforded the 4,5,6,7-tetrahydro-8H-thieno[3,2-c]azepin-8-one (19). In contrast, 7-bromo-5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H-thieno-[3, 2-c]azepin-8-one (20) gave the novel heterocyclic system, 6,7-dihydroazirino[1, 2-a]-thieno[2,3-d]pyridin-8-one (22) under similar conditions.
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M3 - Article
SP - 729
EP - 732
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
ER -