Chemistry of Cyanoacetylenes. Part XIV. One-step Synthesis of Some Ethynyl Heterocycles and Their Reactions with Diazomethane
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概要
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The Ritter reaction of cyano- and chlorocyanoacetylene with appropriate substrates provided a facile one step synthesis of 4,4-dimethyl-2-ethynyloxazoline (<B>5</B>), 4,4,6-trimethyl-2-ethynyl (<B>7</B>) and -2-chloroethynyl-5,6-dihydro-1,3-oxazine (<B>8</B>), 5,5-dimethyl-3-isopropylidene-2-ethynyl- (<B>10</B>) and -2-chloroethynyl-1-pyrroline (<B>11</B>). On treatment with diazomethane, <B>7</B> gave 4,4,6-trimethyl-2-(4-1<I>H</I>-pyrazolyl)- (<B>13</B>) and -2-(3-1<I>H</I>-pyrazolyl)-5,6-dihydro-1,3-oxazine (<B>14</B>) in 42 and 40% yields respectively, while <B>8</B> afforded only 4,4,6-trimethyl-2-[3-(4-chloro-1-methyl)-pyrazolyl]-5,6-dihydro-1,3-oxazine (<B>15</B>) in 52% yield. On the other hand, <B>10</B> gave 5,5-dimethyl-3-isopropylidene-2-(3-1<I>H</I>-pyrazolyl)-1-pyrroline (<B>16</B>) in 64% yield and <B>11</B>, 5,5-dimethyl-3-isopropylidene-2-[3-(4-chloro-1-methyl)-pyrazolyl]-1-pyrroline (<B>17</B>) in 16% yield.
- 公益社団法人 日本化学会の論文
著者
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Eguchi Shoji
Institute Of Applied Organic Chemistry Faculty Of Engineering Nagoya University
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EGUCHI Shoji
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
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Sasaki Tadashi
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
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Sugimoto Michio
Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University
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- Chemistry of Cyanoacetylenes. Part XIV. One-step Synthesis of Some Ethynyl Heterocycles and Their Reactions with Diazomethane