Benzylcarbonyl化合物とFormamideとの反応(第7報) : Desoxybenzoinの反応

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概要

• 論文の詳細を見る

• 4,5-Diphenylpyrimidine (DPP) was obtained on heating deoxybenzoin (DB) with formamide and POCl_3.^<1)> Several deoxybenzoins to generalize this preparative method, and following results were obtained. None from 4,4'-di (CH_3O) DB (I), 3,4-3', 4'-bis (OCH_2O)-DB (II), and 3'-(NH_2)-4-(CH_3O) DB (XIXc) ; 4-(4-CH_3O)-5-(4-NO_2) DPP (V) from 4-(CH_3O)-4'-(NO_2) DB (III), 4-(4-NH_2)-5-(4-CH_3O) DPP (VI) from 4'-(CH_3O)-4-(NO_2) DB (IV), 5-(4-NH_2) DPP (XI_a) from 4'-(NO_2) DB (Xa) ; 5-(3-NO_2) DPP (XIb) from 3'-(NO_2) DB (Xb) ; 4-(4-CH_3O)-5-(3-NH_2) DPP (XIc) from 3'-(NO_2)-4-(CH_3O) DB (Xc) ; 6,8-dimethoxy-3-phenylisoquinoline (XIII) from 3', 5'-di(CH_3O) DB (XII) ; 5-(3,4-di (CH_3O) DPP (XVI) with some 6,7-dimethoxy-3-phenylisoquinoline (XV) from 3', 4'-di(CH_3O) DB (XIV) ; 5-(3-CH_3O)- DPP (XIII), from 3'-(CH_3O) DB (XVII) ; 5-(3-NH_2) DPP (XXa) from 3'-(NH_2) DB (XIXa) ; 5-(3-HO) DPP (XXb) from 3'-(HO) DB (XIXb) ; 4-(4-CH_3O)-5-(3-HO) DPP (XXd) from 3'-(HO)-4-(CH_3O) DB (XIXd). From these results, the following will be concluded : (1) To form isoquinolines, at least two +R groups (e.g. CH_3O) must be substituted in the meta and other positions of benzyl in DB. When there is only one substituent at the meta-position of the benzyl group, even though more effective as NH_2 or OH, isoquinoline ring-closure does not take place but the corresponding pyrimidines are obtained. (2) NO_2 substituent is often reduced to NH_2 in this procedure. (3) The presence of +R substituent at the para-position of the benzoyl group of DB deactivates vates this reaction and -R substituent accelerates it.

• 公益社団法人日本薬学会の論文
• 1970-10-25

著者

• 廣田 喬

  Faculty Of Pharmaceutical Sciences Okayama University

• 大和 正利

  Faculty Of Pharmaceutical Sciences Okayama University

• 大和 正利

  第一薬科大学

• 小山 鷹二

  熊本大学薬学部

• 勝瀬 良樹

  熊本大学薬学部

• 戸田 睦子

  熊本大学薬学部

• 廣田 喬

  熊本大学薬学部

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