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Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation
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| Zeitschriftentitel: | Beilstein Journal of Organic Chemistry |
|---|---|
| Personen und Körperschaften: | , , , , , , |
| In: | Beilstein Journal of Organic Chemistry, 12, 2016, S. 2204-2210 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Beilstein Institut
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| Schlagwörter: |
| author_facet |
Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei |
|---|---|
| author |
Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei |
| spellingShingle |
Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei Beilstein Journal of Organic Chemistry Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation Organic Chemistry |
| author_sort |
zhang, xiaofeng |
| spelling |
Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei 1860-5397 Beilstein Institut Organic Chemistry http://dx.doi.org/10.3762/bjoc.12.211 <jats:p>The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and <jats:italic>N</jats:italic>-substituted maleimide in stereoselective fashion.</jats:p> Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation Beilstein Journal of Organic Chemistry |
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| title |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_unstemmed |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_full |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_fullStr |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_full_unstemmed |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_short |
Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_sort |
stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| topic |
Organic Chemistry |
| url |
http://dx.doi.org/10.3762/bjoc.12.211 |
| publishDate |
2016 |
| physical |
2204-2210 |
| description |
<jats:p>The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and <jats:italic>N</jats:italic>-substituted maleimide in stereoselective fashion.</jats:p> |
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| author_facet | Zhang, Xiaofeng, Pham, Kenny, Liu, Shuai, Legris, Marc, Muthengi, Alex, Jasinski, Jerry P, Zhang, Wei, Zhang, Xiaofeng, Pham, Kenny, Liu, Shuai, Legris, Marc, Muthengi, Alex, Jasinski, Jerry P, Zhang, Wei |
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| description | <jats:p>The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and <jats:italic>N</jats:italic>-substituted maleimide in stereoselective fashion.</jats:p> |
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| spelling | Zhang, Xiaofeng Pham, Kenny Liu, Shuai Legris, Marc Muthengi, Alex Jasinski, Jerry P Zhang, Wei 1860-5397 Beilstein Institut Organic Chemistry http://dx.doi.org/10.3762/bjoc.12.211 <jats:p>The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and <jats:italic>N</jats:italic>-substituted maleimide in stereoselective fashion.</jats:p> Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation Beilstein Journal of Organic Chemistry |
| spellingShingle | Zhang, Xiaofeng, Pham, Kenny, Liu, Shuai, Legris, Marc, Muthengi, Alex, Jasinski, Jerry P, Zhang, Wei, Beilstein Journal of Organic Chemistry, Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation, Organic Chemistry |
| title | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_full | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_fullStr | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_full_unstemmed | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_short | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_sort | stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| title_unstemmed | Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation |
| topic | Organic Chemistry |
| url | http://dx.doi.org/10.3762/bjoc.12.211 |