Reaction of furan-2(3H)-ones with 1,2-binucleophiles

Article abstract of DOI:10.1134/S1070428006090144

Reactions of 5-substituted furan-2(3H)-ones with ethylenediamine, 2-aminoethanol, and o-aminophenol do not stop at the stage of formation of the corresponding 4-oxoalkanoic acid amides but lead to new bi-and tricyclic structures as a result of double intr

Full text of DOI:10.1134/S1070428006090144

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OLTXLGꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢁꢁꢏꢃꢄꢊ1±+ꢋꢇꢄꢀꢆꢐꢏꢄꢊ& 2ꢋꢇꢄ
ꢁꢃꢅꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄSSPꢒꢄꢎꢌꢅꢐ±
ꢎꢌꢎꢃꢄPꢄꢊꢈ+ꢇꢄ+ ꢋꢇꢄꢁꢌꢀꢈ±ꢁꢌꢁꢃꢄPꢄDQGꢄꢁꢌꢁꢆ±ꢁꢌꢂꢐꢄPꢄꢄ
ꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢁꢌꢈꢆ±ꢁꢌꢎꢃꢄPꢄDQGꢄꢁꢌꢎꢐ±ꢂꢌꢀꢃꢄPꢄ
ꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢈꢌꢃꢄEUꢌVꢄꢊꢀ+ꢇꢄ1+ꢋꢌꢄ)RXQGꢇꢄJꢒꢄꢄ
&ꢄꢎꢅꢌꢈꢁꢑꢄ+ꢄꢎꢌꢃꢈꢑꢄ1ꢄꢀꢁꢌꢅꢈꢌꢄ& + 1 2ꢌꢄ&DOFXODWHGꢇꢄJꢒꢄ
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ꢊDꢁ3URS\OꢁꢂꢇꢄꢇꢌꢇꢍꢇꢊꢇꢊDꢁKH[DK\GURꢁꢆ+ꢁS\UURORꢁ
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ꢊ& 2ꢋꢇꢄꢁꢃꢃꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄSSPꢒꢄ
ꢃꢌꢐꢏ±ꢀꢌꢂꢐꢄPꢄꢊꢎ+ꢇꢄ& + ꢋꢇꢄꢁꢌꢀꢀ±ꢁꢌꢁꢃꢄPꢄDQGꢄꢁꢌꢁꢐ±ꢄ
ꢁꢌꢂꢈꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢁꢌꢂꢏ±ꢁꢌꢆꢅꢄPꢄDQGꢄꢁꢌꢎꢃ±
ꢁꢌꢐꢈꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢈꢌꢅꢄEUꢌVꢄꢊꢀ+ꢇꢄ1+ꢋꢌꢄ
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FXODWHGꢇꢄJꢒꢄ&ꢄꢆꢂꢌꢅꢐꢑꢄ+ꢄꢐꢌꢈꢅꢑꢄ1ꢄꢀꢆꢌꢆꢎꢌꢄ
7KXVꢄ ZHꢄ KDYHꢄ VKRZQꢄ WKDWꢄ ꢈꢉVXEVWLWXWHGꢄ IXUDQꢉꢄ
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ꢊꢂꢅJꢋꢌꢄ2LO\ꢄOLTXLGꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢀꢆꢎꢃꢄꢊ& 2ꢋꢇꢄ
ꢀꢃꢎꢃꢄꢊ&±2±&ꢋꢇꢄꢁꢃꢃꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ
ꢇꢄSSPꢒꢄꢅꢌꢂꢈꢄVꢄꢊꢁ+ꢇꢄ0Hꢋꢇꢄꢅꢌꢅꢃ±ꢅꢌꢅꢏꢄPꢄDQGꢄꢅꢌꢁꢈ±ꢅꢌꢈꢈꢄPꢄ
ꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢁꢌꢁꢃ±ꢁꢌꢂꢈꢄPꢄDQGꢄꢁꢌꢈꢈ±ꢁꢌꢎꢃꢄPꢄ
ꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢆꢌꢐꢐ±ꢎꢌꢃꢎꢄPꢄꢊꢂ+ꢇꢄ+
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KH[DFKORUREXWDGLHQHꢌꢄ7KHꢄ +ꢄ 105ꢄ VSHFWUDꢄ ZHUHꢄ
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>ꢆꢇꢄ@R[D]ROꢁꢌꢁRQHꢀ ꢃ,,,Eꢅꢈꢄ<LHOGꢄꢃꢌꢅꢎꢄJꢄꢊꢂꢂJꢋꢌꢄ2LO\ꢄ
OLTXLGꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢀꢆꢎꢈꢄꢊ& 2ꢋꢇꢄꢀꢃꢎꢐꢄꢄ
ꢊ&±2±&ꢋꢇꢄꢁꢃꢃꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄ
ꢊDꢁꢃꢋꢁ0HWK\OSKHQ\OꢅꢁꢂꢇꢄꢇꢌꢇꢍꢇꢊꢇꢊDꢁKH[DK\GURꢁꢆ+ꢁ
S\UUROR>ꢂꢇꢆꢁD@LPLGD]ROꢁꢌꢁRQHꢀ ꢃ,,Dꢅꢈꢄ $ꢄ PL[WXUHꢄ RIꢄꢄ
ꢁꢄPPROꢄRIꢄFRPSRXQGꢄ,DꢇꢄꢁꢄPPROꢄRIꢄHWK\OHQHGLDPLQHꢇꢄ
DQGꢄ ꢃꢌꢅꢄ Jꢄ RIꢄ .8ꢉꢅꢄ LRQꢄ H[FKDQJHUꢄ LQꢄ ꢅꢈꢄ POꢄ RIꢄ DQK\ꢉ
GURXVꢄEHQ]HQHꢄZDVꢄKHDWHGꢄXQGHUꢄUHIOX[ꢄZLWKꢄFRQWLQXꢉ
RXVꢄ UHPRYDOꢄ RIꢄ WKHꢄOLEHUDWHGꢄ ZDWHUꢄ DVꢄD]HRWURSHꢌꢄ7KHꢄ
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SSPꢒꢄꢎꢌꢀꢐꢄPꢄꢊꢈ+ꢇꢄ+
ꢋꢇꢄꢅꢌꢅꢃ±ꢅꢌꢁꢂꢄPꢄDQGꢄꢅꢌꢂꢁ±ꢄ
ꢅꢌꢆꢃꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢁꢌꢁꢏ±ꢁꢌꢂꢈꢄPꢄDQGꢄꢁꢌꢆꢅ±
ꢁꢌꢎꢂꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢌꢄ)RXQGꢇꢄJꢒꢄ&ꢄꢎꢀꢌꢈꢂꢑꢄꢄ
+ꢄꢆꢌꢎꢅꢑꢄ1ꢄꢆꢌꢆꢅꢌꢄ& + 12 ꢌꢄ&DOFXODWHGꢇꢄJꢒꢄ&ꢄꢎꢀꢌꢏꢐꢑꢄꢄ
+ꢄꢆꢌꢐꢀꢑꢄ1ꢄꢆꢌꢂꢈꢌꢄ
ꢊDꢁ3URS\OꢁꢂꢇꢄꢇꢌꢇꢍꢇꢊꢇꢊDꢁKH[DK\GURS\UUROR>ꢂꢇꢆꢁE@ꢁ
>ꢆꢇꢄ@R[D]ROꢁꢌꢁRQHꢀ ꢃ,,,Fꢅꢈꢄ<LHOGꢄꢃꢌꢅꢎꢄJꢄꢊꢂꢂJꢋꢇꢄQ ꢄ ꢄ
DFHWDWH±KH[DQHꢄ ꢊꢅꢒꢀꢋꢄ DVꢄ HOXHQWꢌꢄ <LHOGꢄ ꢃꢌꢅꢏꢄ Jꢄ ꢊꢂꢎJꢋꢌꢄ ꢀꢌꢂꢏꢐꢃꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢀꢆꢐꢈꢄꢊ& 2ꢋꢇꢄꢀꢃꢏꢆꢄꢄ
2LO\ꢄOLTXLGꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢁꢁꢐꢅꢄꢊ1±+ꢋꢇꢄꢀꢆꢏꢏꢄ ꢊ&±2±&ꢋꢇꢄꢁꢃꢃꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄ
ꢊ& 2ꢋꢇꢄꢁꢃꢅꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄSSPꢒꢄ SSPꢒꢄꢃꢌꢐꢅ±ꢀꢌꢎꢃꢄPꢄꢊꢎ+ꢇꢄ& + ꢋꢇꢄꢀꢌꢐꢆ±ꢅꢌꢅꢁꢄPꢄDQGꢄꢅꢌꢁꢅ±
5866,$1ꢄꢄ-2851$/ꢄꢄ2)ꢄꢄ25*$1,&ꢄꢄ&+(0,675<ꢄꢄꢄ9ROꢌꢄꢄꢂꢅꢄꢄꢄ1Rꢌꢄꢄꢐꢄꢄꢄꢅꢃꢃꢆꢄ

5($&7,21ꢄꢄ2)ꢄꢄ)85$1ꢉꢅꢊꢁ+ꢋꢉ21(6ꢄꢄ:,7+ꢄꢄꢀꢇꢅꢉ%,18&/(23+,/(6ꢄ
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QRꢌꢄꢃꢈꢉꢃꢁꢉꢁꢅꢀꢐꢆꢋꢌꢄ
ꢅꢌꢂꢃꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢇꢄꢁꢌꢁꢈ±ꢁꢌꢈꢃꢄPꢄDQGꢄꢁꢌꢆꢃ±
ꢁꢌꢎꢈꢄPꢄꢊꢅ+ꢄHDFKꢇꢄ& + ꢇꢄ& + ꢋꢌꢄ)RXQGꢇꢄJꢒꢄ&ꢄꢆꢁꢌꢎꢀꢑꢄꢄ
+ꢄꢏꢌꢈꢂꢑꢄ1ꢄꢏꢌꢂꢂꢌꢄ& + 12 ꢌꢄ&DOFXODWHGꢇꢄJꢒꢄ&ꢄꢆꢁꢌꢐꢀꢑꢄꢄ
+ꢄꢏꢌꢏꢏꢑꢄ1ꢄꢏꢌꢅꢏꢌꢄ
5()(5(1&(6ꢄ
ꢄDꢁ3URS\OꢁꢆꢇꢂꢇꢄꢇꢄDꢁWHWUDK\GURS\UUROR>ꢂꢇꢆꢁE@ꢁ
>ꢆꢇꢄ@EHQ]R[D]ROꢁꢆꢁRQHꢀ ꢃ,9Fꢅꢈꢄ <LHOGꢄ ꢀꢌꢀꢂꢄ Jꢄ ꢊꢎꢈJꢋꢌꢄ
2LO\ꢄOLTXLGꢌꢄ,5ꢄVSHFWUXPꢇꢄ ꢇꢄFP ꢒꢄꢀꢎꢃꢃꢄꢊ& 2ꢋꢇꢄꢀꢃꢏꢃꢄ
ꢊ&±2±&ꢋꢇꢄꢁꢃꢃꢃ±ꢅꢐꢀꢃꢄꢊ&±+ꢋꢌꢄ +ꢄ105ꢄVSHFWUXPꢇꢄ ꢇꢄ
SSPꢒꢄ ꢃꢌꢏꢆ±ꢀꢌꢎꢏꢄ Pꢄ ꢊꢎ+ꢇꢄ & + ꢋꢇꢄ ꢆꢌꢏꢅ±ꢎꢌꢀꢁꢄ Pꢄ ꢊꢂ+ꢇꢄ
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.KLPꢂꢉ)DUPꢂꢀ=KꢌꢇꢄꢀꢐꢏꢂꢇꢄSꢌꢄꢅꢐꢃꢌꢄ
ꢅꢌꢄ6WH]KNRꢇꢄ 7ꢌ9ꢌꢇꢄ *UDQLNꢇꢄ 9ꢌ*ꢌꢇꢄ *OXVKNRYꢇꢄ 5ꢌ*ꢌꢇꢄ 5RVKFKLꢉꢄ
+
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QDꢇꢄ /ꢌ)ꢌꢇꢄ 3ROH]KDHYDꢇꢄ $ꢌ,ꢌꢇꢄ DQGꢄ 0DVKNRYVNLLꢇꢄ 0ꢌ'ꢌꢇꢄ
.KLPꢂꢉ)DUPꢂꢀ=KꢌꢇꢄꢀꢐꢏꢂꢇꢄSꢌꢄꢏꢅꢁꢌꢄ
&+ ꢋꢌꢄ)RXQGꢇꢄJꢒꢄ&ꢄꢎꢀꢌꢈꢁꢑꢄ+ꢄꢆꢌꢏꢈꢑꢄ1ꢄꢆꢌꢈꢂꢌꢄ& + 12 ꢌꢄ
&DOFXODWHGꢇꢄJꢒꢄ&ꢄꢎꢀꢌꢏꢐꢑꢄ+ꢄꢆꢌꢐꢀꢑꢄ1ꢄꢆꢌꢂꢈꢌꢄ
ꢁꢌꢄ6WH]KNRꢇꢄ 7ꢌ9ꢌꢇꢄ *UDQLNꢇꢄ 9ꢌ*ꢌꢇꢄ *OXVKNRYꢇꢄ 5ꢌ*ꢌꢇꢄ 5RVKFKLꢉꢄ
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QDꢇꢄ /ꢌ)ꢌꢇꢄ 3ROH]KDHYDꢇꢄ $ꢌ,ꢌꢇꢄ DQGꢄ 0DVKNRYVNLLꢇꢄ 0ꢌ'ꢌꢇꢄ
.KLPꢂꢉ)DUPꢂꢀ=KꢌꢇꢄꢀꢐꢏꢂꢇꢄSꢌꢄꢀꢀꢐꢏꢌꢄ
ꢄDꢁ0HWK\OꢁꢆꢇꢂꢇꢄꢇꢄDꢁWHWUDK\GURS\UUROR>ꢂꢇꢆꢁE@ꢁ
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