Unexpected Brønsted Acid‐Catalyzed Domino Reaction of 3‐Hydroxyisoindolin‐1‐ones and N‐tert‐Butyl Hydrazones for the Synthesis of 3‐(Hydrazono)isoindolin‐1‐ones
A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)is...
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| Published in | European journal of organic chemistry Vol. 2018; no. 47; pp. 6733 - 6737 |
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| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
19.12.2018
Wiley Subscription Services, Inc |
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| Abstract | A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of 5w.
3‐(Hydrazono)isoindolin‐1‐one derivatives were synthesized in excellent yields and high chemoselectivities by a Brønsted acid‐catalyzed domino reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction. |
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| AbstractList | A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and
N
‐
tert
‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The
E
‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of
5w
. A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of 5w. 3‐(Hydrazono)isoindolin‐1‐one derivatives were synthesized in excellent yields and high chemoselectivities by a Brønsted acid‐catalyzed domino reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction. A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of 5w. A Bronsted acid-catalyzed aza-Mannich reaction between 3-hydroxyisoindolin-1-ones and N-tert-butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3-(hydrazono)isoindolin-1-one derivatives in excellent yields with high chemoselectivities. The E-configuration of the hydrazone products was determined by X-ray single-crystal diffraction of 5w. |
| Author | He, Xuefeng Zhang, Yaqi He, Wenhuan Zhang, Yuyang Chen, Xiangmeng Chen, Hui‐Xuan Liang, Hao Li, Yongsu Jiang, Xiaoding Cao, Rihui Liu, Gao‐Feng Qiu, Liqin |
| Author_xml | – sequence: 1 givenname: Hui‐Xuan orcidid: 0000-0003-1306-1956 surname: Chen fullname: Chen, Hui‐Xuan organization: Sun Yat‐Sen University – sequence: 2 givenname: Yongsu surname: Li fullname: Li, Yongsu organization: Sun Yat‐Sen University – sequence: 3 givenname: Xuefeng surname: He fullname: He, Xuefeng organization: Sun Yat‐Sen University – sequence: 4 givenname: Yaqi surname: Zhang fullname: Zhang, Yaqi organization: Sun Yat‐Sen University – sequence: 5 givenname: Wenhuan surname: He fullname: He, Wenhuan organization: Sun Yat‐Sen University – sequence: 6 givenname: Hao surname: Liang fullname: Liang, Hao organization: Sun Yat‐Sen University – sequence: 7 givenname: Yuyang surname: Zhang fullname: Zhang, Yuyang organization: Sun Yat‐Sen University – sequence: 8 givenname: Xiaoding surname: Jiang fullname: Jiang, Xiaoding organization: Sun Yat‐Sen University – sequence: 9 givenname: Xiangmeng surname: Chen fullname: Chen, Xiangmeng organization: Sun Yat‐Sen University – sequence: 10 givenname: Rihui surname: Cao fullname: Cao, Rihui organization: Sun Yat‐Sen University – sequence: 11 givenname: Gao‐Feng surname: Liu fullname: Liu, Gao‐Feng organization: Sun Yat‐Sen University – sequence: 12 givenname: Liqin orcidid: 0000-0003-1703-3530 surname: Qiu fullname: Qiu, Liqin email: qiuliqin@mail.sysu.edu.cn organization: Sun Yat‐Sen University |
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| CitedBy_id | crossref_primary_10_1021_acs_orglett_4c02346 crossref_primary_10_1016_j_tetlet_2024_155242 crossref_primary_10_1039_D1OB00017A crossref_primary_10_1002_ange_202012861 crossref_primary_10_1039_D2CC02667H crossref_primary_10_1002_anie_202012861 crossref_primary_10_1021_acs_joc_9b02127 crossref_primary_10_1002_adsc_202100522 |
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| Keywords | DIRECTING GROUP Isoindolinones ENANTIOSELECTIVE SYNTHESIS AMINO ESTERS ACYL KETIMINES Organocatalysis C-H ACTIVATION ASYMMETRIC ORGANOCATALYTIC SYNTHESIS MICHAEL ADDITION Aza-Mannich reaction 3+2 ANNULATION CHIRAL DICARBOXYLIC-ACID CARBONYLATION Homogeneous catalysis Domino reactions |
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| Snippet | A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic... A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N ‐ tert ‐butyl hydrazones was developed. Under the catalysis of the... A Bronsted acid-catalyzed aza-Mannich reaction between 3-hydroxyisoindolin-1-ones and N-tert-butyl hydrazones was developed. Under the catalysis of the racemic... |
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| SubjectTerms | Acids Aza‐Mannich reaction Cascade chemical reactions Catalysis Chemical synthesis Chemistry Chemistry, Organic Domino reactions Homogeneous catalysis Hydrazones Isoindolinones Organocatalysis Phosphoric acid Physical Sciences Science & Technology |
| Title | Unexpected Brønsted Acid‐Catalyzed Domino Reaction of 3‐Hydroxyisoindolin‐1‐ones and N‐tert‐Butyl Hydrazones for the Synthesis of 3‐(Hydrazono)isoindolin‐1‐ones |
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