Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations
Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations
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DOI：
10.1021/acs.joc.1c00206
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发表时间：
2021-04-05
影响因子：
3.6
通讯作者：
Koutentis, Panayiotis A.
中科院分区：
文献类型：
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作者：
Kalogirou, Andreas S.;Kourtellaris, Andreas;Koutentis, Panayiotis A.
2-[(3，5-Dichloro-4H-1，2，6-thiadiazin-4-ylidene)amino]-benzamides通过(I)NaH处理和(II)Pd催化的C-N偶联反应环化成benzo[e][1，2，6]thiadiazino[3，4-b][1，4]diazepin-10(11H)-ones。后者对亲核试剂的行为以及热、氧化和还原条件揭示了3，5-dioxo-4，5-dihydro-3H-benzo[e][1，4]diazepine-2-carbonitrile和2-(4-substituted-1，2，5-thiadiazol-3-yl)quinazolin-4(3H)-ones.的意外转变
2-[(3,5-Dichloro-4H-1,2,6-thiadiazin-4-ylidene)amino]-benzamides are cyclized to benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones via (i) treatment with NaH and via (ii) Pd-catalyzed C-N coupling. The behavior of the latter toward nucleophiles and thermal, oxidative, and reductive conditions revealed unexpected transformations to 3,5-dioxo-4,5-dihydro-3H-benzo[e][1,4]diazepine-2-carbonitrile and 2-(4-substituted-1,2,5-thiadiazol-3-yl)quinazolin-4(3H)-ones.