Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Kadina, Anastasia P.; Новиков, Михаил С.; Khlebnikov, Alexander F.; Magull, Jörg

doi:10.1007/s10593-008-0077-6

Chem Heterocycl Comp

2008

DOI: 10.1007/s10593-008-0077-6

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Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Anastasia P. Kadina

Михаил С. Новиков

Alexander F. Khlebnikov

et al.

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Cited by 9 publications

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“…The realization of this chain of transformations leads us to assign it as a "domino" process of consecutive reactions [4][5][6].…”

mentioning

confidence: 99%

An example of a domino reaction in the synthesis of pyrazolo[1,5-a]pyrimidine derivative

Danagulyan

Boyakhchyan

Kirakosyan

2010

Chem Heterocycl Comp

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Condensation of ethyl 3-aminopyrazole-4-carboxylate (1) with ethyl ethoxymethylenecyanoacetate (2) was carried out with the aim of preparing diethyl 7-aminopyrazolo[1,5-a]pyrimidine-3,6-dicarboxylate (3) and subsequent study of its C-C recyclization [1] to the isomeric 6-carbamoyl-7-hydroxypyrazolopyrimidine but the reaction did not go to completion. From 1 H NMR spectra (including experiments using the NOESY method) it was clear that a mixture of compounds including both the cyclization product 3 and the uncyclized condensation adduct ethyl 3-[(2-cyano-3-ethoxy-3-oxoprop-1-en-1-yl)amino]-1H-pyrazole-4-carboxylate (4) had been obtained. However, in basic medium both the condensed pyrazolopyrimidine 3 and the cyano derivative 4 were readily converted in high yield to the 6-carbamoyl-7-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylic acid (5). CO 2 H 1 2 4 3 5 NaOHBearing in mind that the starting 3-aminopyrazole 1 is synthesized by reaction of hydrazine with the same ethoxymethylenecyanoacetate ester 2 [2] we believed that compound 5 could be prepared directly by

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“…The realization of this chain of transformations leads us to assign it as a "domino" process of consecutive reactions [4][5][6].…”

mentioning

confidence: 99%

An example of a domino reaction in the synthesis of pyrazolo[1,5-a]pyrimidine derivative

Danagulyan

Boyakhchyan

Kirakosyan

2010

Chem Heterocycl Comp

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ChemInform Abstract: Azirino[c]imidazolyl Ylides in the Domino Reaction of 2,2‐Dialkyl‐4,6‐diaryl‐1,3‐diazabicyclo[3.1.0]hex‐3‐enes with Dichlorocarbenes. Synthesis of (1RS,5SR,6RS)‐4‐ (Alk‐1‐enyl)‐1,5‐diaryl‐3,7,7‐trichloro‐2,4‐diazabicyclo [4.1.0]hept‐2‐enes.

et al. 2009

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Fused pyrimidine derivatives R 0515Azirino[c]imidazolyl Ylides in the Domino Reaction of 2,2-Dialkyl-4,6-diaryl--1,3-diazabicyclo[3.1.0]hex-3-enes with Dichlorocarbenes. Synthesis of (1RS,5SR,6RS)-4-(Alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes. -Quantum-chemical calculations using the DFT B3LYP/ 6-31G(d) method confirm that the mechanism of the presented reaction includes the formation of azirino[c]imidazolium ylides and coordinated opening of the imidazole and aziridine rings with subsequent cyclization and dichloropropane formation. Mechanism and calculations are discussed in detail. The structure of product (IIIa) is proved by X-ray analysis. -(KADINA, A. P.; NOVIKOV, M. S.; KHLEBNIKOV*, A. F.; MAGULL, J.; Chem. Heterocycl. Compd. (N. Y.) 44 (2008) 5, 576-584; Fac. Chem., St. Petersburg State Univ., St. Petersburg 198504, Russia; Eng.) -H. Haber 23-158

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Rh(II)-Catalysed reactions of 2H-azirines with ethyl 2-acyl-2-diazoacetates. Synthesis of novel photochromic oxazines

Khlebnikov

Новиков

Хлебников

et al. 2009

Tetrahedron Letters

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Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Cited by 9 publications

References 23 publications

An example of a domino reaction in the synthesis of pyrazolo[1,5-a]pyrimidine derivative

An example of a domino reaction in the synthesis of pyrazolo[1,5-a]pyrimidine derivative

ChemInform Abstract: Azirino[c]imidazolyl Ylides in the Domino Reaction of 2,2‐Dialkyl‐4,6‐diaryl‐1,3‐diazabicyclo[3.1.0]hex‐3‐enes with Dichlorocarbenes. Synthesis of (1RS,5SR,6RS)‐4‐ (Alk‐1‐enyl)‐1,5‐diaryl‐3,7,7‐trichloro‐2,4‐diazabicyclo [4.1.0]hept‐2‐enes.

Rh(II)-Catalysed reactions of 2H-azirines with ethyl 2-acyl-2-diazoacetates. Synthesis of novel photochromic oxazines

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