Microwave assisted aminocatalyzed [3+2] annulation between alpha-iminonitriles and succinaldehyde: synthesis of pyrrole-3-methanols and related polycyclic ring systems

Mir Nisar A.; Choudhary Sachin; Ramaraju Panduga; Singh Deepika; Kumar Indresh

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Microwave assisted aminocatalyzed [3+2] annulation between alpha-iminonitriles and succinaldehyde: synthesis of pyrrole-3-methanols and related polycyclic ring systems

机译：微波辅助氨基催化[3 + 2]环素在α-伊宁腈和肉豆蔻醛之间：合成吡咯-3-甲醇和相关多环环系统

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A quick and highly efficient method for the synthesis of substituted pyrrole-3-methanols from alpha-iminonitriles and succinaldehyde under microwave irradiation is reported. This one-pot method involves aminocatalyzed direct Mannich reaction-cyclization-dehydrocyanation followed by NaBH4 reduction sequence in good yields (up to 75%). Further applications of this method are demonstrated through the rapid synthesis of polycyclic heterocycles such as pyrrolo-dihydrochromene and pyrrolo-dihydroquinoline compounds.

机译：报道了一种快速且高效地，用于在微波辐射下合成来自α-伊宁腈和肉豆蔻醛的取代吡咯-3-甲醇的方法。这种单壶方法涉及氨基催化直接曼尼希反应环化 - 脱水氰化，然后得到NaBH4还原序列，产率良好（高达75％）。通过快速合成多环杂环如吡咯 - 二羟基丙烯喹和吡咯 - 二氢喹啉化合物，证明了该方法的进一步应用。

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来源
《RSC Advances》 |2016年第46期|共9页
作者
Mir Nisar A.; Choudhary Sachin; Ramaraju Panduga; Singh Deepika; Kumar Indresh;
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作者单位

Birla Inst Technol &

Sci Dept Chem Pilani 333031 Rajasthan India;

Birla Inst Technol &

Sci Dept Chem Pilani 333031 Rajasthan India;

Birla Inst Technol &

Sci Dept Chem Pilani 333031 Rajasthan India;

IIIM CSIR Lab Instrumentat Div Jammu 180001 India;

Birla Inst Technol &

Sci Dept Chem Pilani 333031 Rajasthan India;

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正文语种 eng
中图分类化学;
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1. Microwave assisted aminocatalyzed [3+2] annulation between alpha-iminonitriles and succinaldehyde: synthesis of pyrrole-3-methanols and related polycyclic ring systems [J] . Mir Nisar A., Choudhary Sachin, Ramaraju Panduga, RSC Advances . 2016,第46期

机译：微波辅助氨基催化[3 + 2]环素在α-伊宁腈和肉豆蔻醛之间：合成吡咯-3-甲醇和相关多环环系统
2. Erratum: A facile three-component [3+2]-cycloaddition/annulation domino protocol for the regio- and diastereoselective synthesis of novel penta- and hexacyclic cage systems, involving the generation of two heterocyclic rings and five contiguous stereocenters (Tetrahedron (2011) 67 (3132-3139)) [J] . Kumar R.S., Osman H., Perumal S., Tetrahedron . 2012,第19期

机译：勘误：一种新颖的五和六环笼系统的区域和非对映选择性合成的三组分[3 + 2]-环加成/环线多米诺协议，涉及到两个杂环和五个连续立体中心的生成（Tetrahedron（2011） 67（3132-3139））
3. A facile three-component [3+2]-cycloaddition/annulation domino protocol for the regio- and diastereoselective synthesis of novel penta- and hexacyclic cage systems, involving the generation of two heterocyclic rings and five contiguous stereocenters [J] . Suresh Kumar R., Osman H., Perumal S., Tetrahedron . 2011,第17期

机译：一种用于新的五环和六环笼系统的区域和非对映选择性合成的简便的三组分[3 + 2]-环加成/环抱多米诺协议，涉及两个杂环和五个连续立体中心的生成
4. Optimization of Pyran Ring Annulation in the Synthesis of Acronycine and Its Derivatives [C] . R. F. Fatykhov, A. K. Inyutina, I. A. Khalymbadzha, International Conference on Modern Synthetic Methodologies for Creating Drugs and Functional Materials . 2019

机译：吡喃环环节在合成的吡喃环环节中的优化及其衍生物
5. (3+2) Annulation Reactions of Azaoxyallyl Cations: Synthesis of Pyrroloindolines and Imidazolones [D] . DiPoto, Maria C. 2018

机译：（3 + 2）氮氧基烯丙基阳离子的环化反应：吡咯啉二环和咪唑酮的合成
6. ASYMMETRIC SYNTHESIS OF THE ABCD RING SYSTEM OF DAPHNILACTONE B VIA A TANDEM DOUBLE INTRAMOLECULAR 4+2/3+2 CYCLOADDITION STRATEGY [O] . Scott E. Denmark, Son T. Nguyen, Ramil Y. Baiazitov -1

机译：通过串联双分子间4 + 2 / 3 + 2循环加载策略对达菲内酯B的ABCD环系统进行不对称合成
7. Microwave-assisted reactions of allenic esters: [3+2] annulations and allenoate-Claisen rearrangement [O] . Susana M. M. Lopes, Bruna S. Santos, Francisco Palacios, 2009

机译：微生物辅助的丙二醇酯反应：[3 + 2]环和allenoate-Claisen重排

Microwave assisted aminocatalyzed [3+2] annulation between alpha-iminonitriles and succinaldehyde: synthesis of pyrrole-3-methanols and related polycyclic ring systems

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