2021
DOI: 10.1021/acs.joc.1c00993
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Inverse Electron-Demand Aza-Diels–Alder Reaction of Cyclic Enamides with 1,2-Diaza-1,3-dienes in Situ Generated from α-Halogeno Hydrazones: Access to Fused Polycyclic Tetrahydropyridazine Derivatives

Abstract: An efficient inverse electron-demand aza-Diels− Alder reaction of cyclic enamides and 1,2-diaza-1,3-dienes, which could be readily formed in situ from α-halogeno hydrazones and a base, has been successfully developed. With the developed approach, a wide range of fused polycyclic tetrahydropyridazines were smoothly obtained in up to 99% yield under benign reaction conditions. This reaction concept was also extended to acyclic enamide substrates for accessing 1,4,5,6-tetrahydropyridazines. A gram-scale experimen… Show more

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Cited by 13 publications
(7 citation statements)
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“…White solid (681 mg, 65% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 (d,J = 8.3 Hz,2H),7.93 (d,J = 8.6 Hz,2H),7.45 (d,J = 8.6 Hz,2H) C{ 1 H} NMR (100 MHz,CDCl 3 ) δ 196.8,171.6,146.8,139.7,135.7,130.6,129.6,129.0,127.6,126.2,29.7,29.7,19.9. HRMS (ESI) m/z [M + H] + : calcd for: C 17 H 14 ClO 3 301.0626.…”
Section: -(2-(3-bromobenzoyl)cyclopropyl)benzonitrile (1x)mentioning
confidence: 99%
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“…White solid (681 mg, 65% yield). 1 H NMR (400 MHz, CDCl 3 ) δ 8.06 (d,J = 8.3 Hz,2H),7.93 (d,J = 8.6 Hz,2H),7.45 (d,J = 8.6 Hz,2H) C{ 1 H} NMR (100 MHz,CDCl 3 ) δ 196.8,171.6,146.8,139.7,135.7,130.6,129.6,129.0,127.6,126.2,29.7,29.7,19.9. HRMS (ESI) m/z [M + H] + : calcd for: C 17 H 14 ClO 3 301.0626.…”
Section: -(2-(3-bromobenzoyl)cyclopropyl)benzonitrile (1x)mentioning
confidence: 99%
“…: 221.4−222.2 °C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.31 (d,J = 8.7 Hz,1H),7.92 (s,1H),3H),2H),2H),3H),4H),6.87 (dd,J = 10.3,4.0 Hz,1H),5.30 (s,1H),2.79 (dd,J = 18.1,1.7 Hz,1H),2H),1H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 146.…”
Section: -(2-(3-bromobenzoyl)cyclopropyl)benzonitrile (1x)mentioning
confidence: 99%
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“…The reaction also works perfectly using cyclic enamide to provide structurally important fused polycyclic tetrahydronaphthalene-tetrahydropyridazines 123 . In both cases, the cycloaddition proceeds with excellent regio- and diastereoselectivity [ 53 ], and both enamide and diazadiene can have electron donor or acceptor groups that are well tolerated.…”
Section: Synthesis Of Heterocycles From 12-diaza-13-dienesmentioning
confidence: 99%
“…In contrast, the systematic application with α,β-unsaturated thioesters as CS dienophiles has not been seen in previous reports. As a continuation of the selection of α-halogeno hydrazones as building blocks to construct structurally diverse heterocyclic compounds, the highly regioselective inverse electron-demand aza-Diels–Alder reaction of 1,2-diaza-1,3-dienes generated in situ from α-halogeno hydrazones with α,β-unsaturated thioesters has been developed recently in our laboratory (Scheme b). Herein, we disclose our research output.…”
Section: Introductionmentioning
confidence: 99%