An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

Prashant Mujumdar; Alexander Sapegin; Mikhail Dorogov; Mikhail Krasavin

doi:10.1016/j.tetlet.2014.06.104

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

Prashant Mujumdar, Alexander Sapegin, Mikhail Dorogov, Mikhail Krasavin

Research output: Contribution to journal › Article › Research › peer-review

4 Citations (Scopus)

Abstract

We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

Original language	English
Pages (from-to)	5732-5735
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2014.06.104
Publication status	Published - 15 Oct 2014
Externally published	Yes

Keywords

Atom efficiency
Intramolecular alkylation
Lead-likeness
Privileged structure
Propargylamine
Pyrazole
Sonogashira coupling
Ynone

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10.1016/j.tetlet.2014.06.104

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title = "An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones",

abstract = "We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.",

keywords = "Atom efficiency, Intramolecular alkylation, Lead-likeness, Privileged structure, Propargylamine, Pyrazole, Sonogashira coupling, Ynone",

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T1 - An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

AU - Mujumdar, Prashant

AU - Sapegin, Alexander

AU - Dorogov, Mikhail

AU - Krasavin, Mikhail

PY - 2014/10/15

Y1 - 2014/10/15

N2 - We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

AB - We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

KW - Atom efficiency

KW - Intramolecular alkylation

KW - Lead-likeness

KW - Privileged structure

KW - Propargylamine

KW - Pyrazole

KW - Sonogashira coupling

KW - Ynone

UR - http://www.scopus.com/inward/record.url?scp=84908395346&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.06.104

DO - 10.1016/j.tetlet.2014.06.104

M3 - Article

AN - SCOPUS:84908395346

SN - 0040-4039

VL - 55

SP - 5732

EP - 5735

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

Abstract

Keywords

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