Literature DB >> 26488671

Benzoic Acid Catalyzed Annulations of α-Amino Acids and Aromatic Aldehydes Containing an ortho-Michael Acceptor: Access to 2,5-Dihydro-1H-benzo[c]azepines and 10,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines.

Mi Tang, Lingfeng Tong, Lei Ju, Wanwan Zhai, Yang Hu, Xinhong Yu1.   

Abstract

A novel one-pot efficient synthesis of 2,5-dihydro-1H-benzo[c]azepines and 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a]azepines from α-amino acids and aromatic aldehydes containing an ortho-Michael acceptor is reported via decarboxylative annulations without metal catalysts in yields of 52-91%. Under microwave irradiation, this protocol provides rapid access to polycyclic ring systems (only 5 min in most cases).

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Year:  2015        PMID: 26488671     DOI: 10.1021/acs.orglett.5b02484

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors:  Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2020-01-27       Impact factor: 6.005

2.  An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2016-01-19       Impact factor: 6.005

3.  Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.

Authors:  Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

4.  Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors:  Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal:  Org Lett       Date:  2018-06-25       Impact factor: 6.005

5.  Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.

Authors:  YoungKu Kang; Daniel Seidel
Journal:  Org Lett       Date:  2016-08-10       Impact factor: 6.005

6.  Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.

Authors:  Zhengbo Zhu; Daniel Seidel
Journal:  Org Lett       Date:  2017-05-16       Impact factor: 6.005

7.  Traceless Redox-Annulations of Alicyclic Amines.

Authors:  Dillon R L Rickertsen; Longle Ma; Anirudra Paul; Khalil A Abboud; Daniel Seidel
Journal:  SynOpen       Date:  2020-12-16
  7 in total

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