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Literature DB >> 20160922

Synthesis of pyrrolo[1,3]diazepines by a dipolar cycloaddition - retro-Mannich domino reaction.

Mary Liang¹, Cecilia Saiz, Chiara Pizzo, Peter Wipf.

Abstract

Microwave irradiation facilitated the synthesis of 4-arylthio-3-oxazolin-5-ones from ethyl cyanoformate, thiophenol, and cyclic ketones. Subsequent decarboxylation and in situ [3+2] cycloaddition provided novel 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-c][1,3]diazepine scaffolds after a spontaneous retro-Mannich domino reaction.

Entities: Chemical Disease Species

Year: 2009 PMID： 20160922 PMCID： PMC2770875 DOI： 10.1016/j.tetlet.2009.09.107

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

11 in total

1. Synthesis of 1,3-dioxo-hexahydropyrido[1,2-c][1,3]diazepine carboxylates, a new bicyclic skeleton formed by ring expansion-RCM methodology.

Authors: Nicolai Dieltiens; Diederica D Claeys; Bart Allaert; Francis Verpoort; Christian V Stevens
Journal: Chem Commun (Camb) Date: 2005-08-04 Impact factor: 6.222

2. Formation of macrocycles via ring-closing olefin metathesis.

Authors: C W Lee; R H Grubbs
Journal: J Org Chem Date: 2001-10-19 Impact factor: 4.354

3. A unique ring-expanded acyclic nucleoside analogue that inhibits both adenosine deaminase (ADA) and guanine deaminase (GDA; guanase): synthesis and enzyme inhibition studies of 4,6-diamino-8H-1-hydroxyethoxymethyl-8-iminoimidazo[4,5-e][1,3]diazepine.

Authors: L Wang; R S Hosmane
Journal: Bioorg Med Chem Lett Date: 2001-11-19 Impact factor: 2.823

4. Systematic study of the synthesis of macrocyclic dipeptide beta-turn mimics possessing 8-, 9-, and 10- membered rings by ring-closing metathesis.

Authors: Ramesh Kaul; Simon Surprenant; William D Lubell
Journal: J Org Chem Date: 2005-05-13 Impact factor: 4.354

Review 1. Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives.

Authors: Mohsine Driowya; Aziza Saber; Hamid Marzag; Luc Demange; Khalid Bougrin; Rachid Benhida
Journal: Molecules Date: 2016-08-09 Impact factor: 4.411

1 in total

Synthesis of pyrrolo[1,3]diazepines by a dipolar cycloaddition - retro-Mannich domino reaction.

1. Synthesis of 1,3-dioxo-hexahydropyrido[1,2-c][1,3]diazepine carboxylates, a new bicyclic skeleton formed by ring expansion-RCM methodology.

2. Formation of macrocycles via ring-closing olefin metathesis.

3. A unique ring-expanded acyclic nucleoside analogue that inhibits both adenosine deaminase (ADA) and guanine deaminase (GDA; guanase): synthesis and enzyme inhibition studies of 4,6-diamino-8H-1-hydroxyethoxymethyl-8-iminoimidazo[4,5-e][1,3]diazepine.

4. Systematic study of the synthesis of macrocyclic dipeptide beta-turn mimics possessing 8-, 9-, and 10- membered rings by ring-closing metathesis.

Review 5. Multicomponent domino reactions for the synthesis of biologically active natural products and drugs.

6. Possible ligand-receptor interactions for NK1 antagonists as observed in their crystal structures.

7. Diversity-oriented synthesis of azaspirocycles.

8. Asymmetric synthesis of 8-aminoindolizidine from chiral 2-pyrroleimines.

Review 9. Muscarine, imidazole, oxazole and thiazole alkaloids.

10. Ring closing enyne metathesis: control over mode selectivity and stereoselectivity.

Review 1. Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives.