(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans-Reference-Cited by-同舟云学术

(3 + 3) Annulation of acetoxy allenoates with enolisable carbonyl substrates leading to fused pyrans

Published:2023 Issue:24 Volume:21 Page:5021-5032
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Debnath Shubham¹,Chauhan Sachin¹,Kumara Swamy K. C.¹^ORCID

Affiliation:

1. School of Chemistry, University of Hyderabad, Hyderabad 500 046, Telangana, India

Abstract

Lewis base-controlled (3 + 3) annulation of δ-acetoxy allenoates with N-Boc-oxindole, benzofuranone, or pyrazolone affords fused pyrans; the base DBU gives pyrans, while DMAP affords dihydropyrans.

Funder

Science and Engineering Research Board

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/OB/D3OB00597F

Reference74 articles.

1. N.Krause and A. S.Hashmi , Modern Allene Chemistry , Wiley-VCH , 2004

2. Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses

3. [4+2] and [4+3] catalytic cycloadditions of allenes

4. [2+2+1] Cyclization of allenes

5. Cyclization reactions of bis(allenes) for the synthesis of polycarbo(hetero)cycles

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