An expedient and new synthesis of pyrrolo[1,2-<i>b</i>]pyridazine derivatives

Sagyam, Rajeshwar Reddy; Buchikonda, Ravinder; Pitta, Jaya Prakash; Himabindu, V.; Padi, Pratap Reddy; Ghanta, Mahesh Reddy

doi:10.3762/bjoc.5.66

Cited by 4 publications

(1 citation statement)

References 24 publications

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“…As a result, considerable efforts have been devoted to developing efficient synthetic approaches for this privileged structure 7c,7e,8a,8b. One of the most used methods reported before for the assembly of pyrrolo[1,2‐ b ]pyridazine moieties typically relied on condensation reactions, such as the condensation of cyanoacetic hydrazide with nitriles9 and the condensation of oxazolo[3,2‐ b ]pyridazinium perchlorates with malononitrile, ethyl cyanoacetate or ethyl malonate 10.…”

Section: Introductionmentioning

confidence: 99%

A One‐Pot Copper(II)‐Catalyzed Tandem Synthesis of 2‐Substituted Pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones

Tan

Xiang

2015

Eur J Org Chem

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A one‐pot copper(II)‐catalyzed tandem synthesis of 2‐substituted pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones from N‐aminopyrroles was developed. This tandem reaction involves a Conrad–Limpach‐type reaction, including the thermal condensation of N‐aminopyrroles with the carbonyl group of β‐oxo esters followed by the cyclization of Schiff base intermediates. Compared to the traditional Conrad–Limpach quinoline synthesis, we herein successfully applied copper(II) as a catalyst in this transformation to furnish 2‐substituted pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones for the first time. Most of the substrates bearing electron‐donating (EDG) and electron‐withdrawing (EWG) groups worked well with this procedure. The corresponding products could be converted directly into diverse pyrrolo[1,2‐b]pyridazine for drug discovery and materials science.

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Section: Introductionmentioning

confidence: 99%

A One‐Pot Copper(II)‐Catalyzed Tandem Synthesis of 2‐Substituted Pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones

Tan

Xiang

2015

Eur J Org Chem

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A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling–isomerization–condensation reaction

Wang

Tan

et al. 2013

Org. Biomol. Chem.

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Recent advances in the chemistry of pyridazine — an important representative of six-membered nitrogen heterocycles

Sergeev¹,

Nenajdenko²

2020

Russ. Chem. Rev.

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The review is devoted to recent advances in the chemistry of pyridazine — a six-membered heterocycle containing two nitrogen atoms in adjacent positions. The practical significance of title compounds is demonstrated and published data of the last decade devoted to them are considered systematically. The modern synthetic approaches to pyridazine derivatives are described in detail, analyzed and classified according to the precursor molecules involved in ring closure. The chemical properties of pyridazines are considered, including both reactions of the diazine ring and reactions of various substituents attached to the ring. Particular attention is given to the application of some pyridazine derivatives as pharmaceuticals, optical materials and ligands for catalysis. The bibliography includes 180 references.

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An expedient and new synthesis of pyrrolo[1,2-b]pyridazine derivatives

Cited by 4 publications

References 24 publications

A One‐Pot Copper(II)‐Catalyzed Tandem Synthesis of 2‐Substituted Pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones

A One‐Pot Copper(II)‐Catalyzed Tandem Synthesis of 2‐Substituted Pyrrolo[1,2‐b]pyridazin‐4(1H)‐ones

A novel convenient approach towards pyrrolo[1,2-b]pyridazines through a domino coupling–isomerization–condensation reaction

Recent advances in the chemistry of pyridazine — an important representative of six-membered nitrogen heterocycles

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