Polycyclic N-Hetero Compounds. XVI. Reactions of Benzyl Ketones with Formamide or Acetamide

Polycyclic N-Hetero Compounds. XVI. Reactions of Benzyl Ketones with Formamide or Acetamide

Reaction of α-acyl-α-(m-chlorophenyl) acetonitrile (II) with formamide gave enamines (III) and 4-aminopyrimidines (IV). III could be converted to IV by the same treatment with formamide. 4-Acetamido-5-(3, 5-dimethylphenyl) pyrimidine (Ve) gave 1, 3, 10-triazaphenanthrene (VI) with polyphosphoric aci...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1978/01/25, Vol.26(1), pp.245-250
Hauptverfasser: HIROTA, TAKASHI, KOYAMA, TAKAJI, NANBA, TETSUTO, YAMATO, MASATOSHI, MATSUMURA, TAKAFUMI
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Bischler-Napieralski reaction
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container_end_page 250
container_issue 1
container_start_page 245
container_title Chemical & pharmaceutical bulletin
container_volume 26
creator HIROTA, TAKASHI
KOYAMA, TAKAJI
NANBA, TETSUTO
YAMATO, MASATOSHI
MATSUMURA, TAKAFUMI
description Reaction of α-acyl-α-(m-chlorophenyl) acetonitrile (II) with formamide gave enamines (III) and 4-aminopyrimidines (IV). III could be converted to IV by the same treatment with formamide. 4-Acetamido-5-(3, 5-dimethylphenyl) pyrimidine (Ve) gave 1, 3, 10-triazaphenanthrene (VI) with polyphosphoric acid, although cyclization of m-chloro-(Va) and m-methyl-(Vd) phenyl derivatives were unsuccessful (Chart 1). Reactions of α-acyl-α-(3, 5-dimethoxyphenyl) acetonitrile (VII) with acetamide gave 6-alkyl-5-(3, 5-dimethoxyphenyl)-2-methyl-4 (3H)-pyrimidinone (VIII) which were converted to 4-chloro derivatives (X) with POCl3. Treatment of 3, 5-dimethoxybenzyl alkyl ketones (XI) with acetamide gave 3-alkyl-1-methylisoquinolines (XII) and analogous reaction of 3, 4-methylenedioxyphenylacetone (XIV) gave naphthalene derivative (XV) (Chart 2).
doi_str_mv 10.1248/cpb.26.245
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Reactions of α-acyl-α-(3, 5-dimethoxyphenyl) acetonitrile (VII) with acetamide gave 6-alkyl-5-(3, 5-dimethoxyphenyl)-2-methyl-4 (3H)-pyrimidinone (VIII) which were converted to 4-chloro derivatives (X) with POCl3. Treatment of 3, 5-dimethoxybenzyl alkyl ketones (XI) with acetamide gave 3-alkyl-1-methylisoquinolines (XII) and analogous reaction of 3, 4-methylenedioxyphenylacetone (XIV) gave naphthalene derivative (XV) (Chart 2).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.26.245</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Bischler-Napieralski reaction</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1978/01/25, Vol.26(1), pp.245-250</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1978</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3365-80a332b3df1ec70fa1721ba8804aa6f96c197b45efa674b066045834b8ede6503</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids></links><search><creatorcontrib>HIROTA, TAKASHI</creatorcontrib><creatorcontrib>KOYAMA, TAKAJI</creatorcontrib><creatorcontrib>NANBA, TETSUTO</creatorcontrib><creatorcontrib>YAMATO, MASATOSHI</creatorcontrib><creatorcontrib>MATSUMURA, TAKAFUMI</creatorcontrib><title>Polycyclic N-Hetero Compounds. 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title Polycyclic N-Hetero Compounds. XVI. Reactions of Benzyl Ketones with Formamide or Acetamide
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