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布朗斯台德酸介导的环化-脱磺酰化/还原序列：一种简便合成吡嗪并异喹啉和吡啶并吡嗪的方法。

Brønsted acid-mediated cyclization-dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines.

作者信息

Rao Ramana Sreenivasa, Ramanathan Chinnasamy Ramaraj

机构信息

Department of Chemistry, Pondicherry University, Puducherry - 605 014, India.

出版信息

Beilstein J Org Chem. 2017 Mar 7;13:428-440. doi: 10.3762/bjoc.13.46. eCollection 2017.

DOI:10.3762/bjoc.13.46
PMID:28382181
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5355893/
Abstract

An efficient and alternative synthetic approach has been developed to prepare various -(arylethyl)piperazine-2,6-diones from 4-benzenesulfonyliminodiacetic acid and primary amines using carbonyldiimidazole in the presence of a catalytic amount of DMAP at ambient temperature. Piperazine-2,6-diones are successfully transformed to pharmaceutically useful pyridopyrazines or pyrazinoisoquinolines and ene-diamides via an imide carbonyl group activation strategy using a Brønsted acid. Subsequent dehydrosulfonylation reactions of the ene-diamides, in a one pot manner, smoothly transformed them to substituted pyrazinones. A concise synthesis of praziquantel () has also been achieved through this method.

摘要

已经开发出一种高效的替代合成方法，在环境温度下，使用羰基二咪唑，在催化量的4-二甲氨基吡啶存在下，由4-苯磺酰基亚氨基二乙酸和伯胺制备各种β-(芳基乙基)哌嗪-2,6-二酮。哌嗪-2,6-二酮通过使用布朗斯特酸的酰亚胺羰基活化策略成功转化为药学上有用的吡啶并吡嗪或吡嗪并异喹啉和烯二酰胺。烯二酰胺的后续脱磺酰化反应以一锅法顺利地将它们转化为取代的吡嗪酮。通过该方法也实现了吡喹酮()的简洁合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/8f4af2b8af42/Beilstein_J_Org_Chem-13-428-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/22f7c167eb4b/Beilstein_J_Org_Chem-13-428-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/1ddce8c5a439/Beilstein_J_Org_Chem-13-428-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/68ca1159b58d/Beilstein_J_Org_Chem-13-428-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/3d707bc3f8c3/Beilstein_J_Org_Chem-13-428-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/0739c0f6cec4/Beilstein_J_Org_Chem-13-428-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/c9638e460d3c/Beilstein_J_Org_Chem-13-428-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/71abff0be80d/Beilstein_J_Org_Chem-13-428-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/dd48ee0ce717/Beilstein_J_Org_Chem-13-428-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/3951d4eb43da/Beilstein_J_Org_Chem-13-428-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/a223127aec05/Beilstein_J_Org_Chem-13-428-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/8f4af2b8af42/Beilstein_J_Org_Chem-13-428-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/22f7c167eb4b/Beilstein_J_Org_Chem-13-428-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/1ddce8c5a439/Beilstein_J_Org_Chem-13-428-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/68ca1159b58d/Beilstein_J_Org_Chem-13-428-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/3d707bc3f8c3/Beilstein_J_Org_Chem-13-428-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/0739c0f6cec4/Beilstein_J_Org_Chem-13-428-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/c9638e460d3c/Beilstein_J_Org_Chem-13-428-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/71abff0be80d/Beilstein_J_Org_Chem-13-428-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/dd48ee0ce717/Beilstein_J_Org_Chem-13-428-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/3951d4eb43da/Beilstein_J_Org_Chem-13-428-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/a223127aec05/Beilstein_J_Org_Chem-13-428-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21e2/5355893/8f4af2b8af42/Beilstein_J_Org_Chem-13-428-g012.jpg

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