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Zaima, T.; Matsuno, Chikashi; Mitsuhashi, Keiryo

doi:10.1246/nikkashi.1983.152

Cited by 4 publications

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“…Compound 133 was also found to react with dialkyl acetylenedicarboxylates to give tetraalkyl 7-azabicyclo[2.2.1]hept-2-ene-1,2,3,4-carboxylates. 130 1-Iodo-2-acetoxy- heptane derivative designed and synthesized as a potential biological agent. 109 The cocaine analogue 106 was prepared to investigate the structureactivity relationships (SAR) of local anesthetics.…”

Section: E Miscellaneous Reactionsmentioning

confidence: 99%

“…Compound 133 was also found to react with dialkyl acetylenedicarboxylates to give tetraalkyl 7-azabicyclo[2.2.1]hept-2-ene-1,2,3,4-carboxylates. 130 1-Iodo-2-acetoxy-8-methyl-8-azabicyclo[3.2.1]octan-3-one (136) was reductively transformed into 7-azabicyclo[2.2.1]heptane (137) with lithium aluminum hydride. 131 The structural assignment of the 1-(hydroxymethyl)-2R-hydroxy-7-methyl-7-azabicyclo-[2.2.1]heptane (137) was determined spectroscopically (IR, NMR, and mass spectrometry) and by chemical transformation into 1-methyl-2R-hydroxy-7-methyl-7-azabicyclo[2.2.1]heptane 138 (Scheme 34).…”

Section: E Miscellaneous Reactionsmentioning

confidence: 99%

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Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes

1996

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ContentsI. Introduction 1179 II. Preparation of 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes by the [4+2] Cycloaddition Reaction 1179 A. Lewis Acid Catalyzed Reactions 1181 B. High-Pressure and Ultrasound Reactions 1182 C. Reactions with Acetylene Equivalents 1183 D. Miscellaneous Reactions 1183 III. Chemistry of the 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes 1184 A. Synthesis of Substituted Pyrroles 1184 B. Synthesis of Substituted Arene Derivatives 1185 C. Synthesis of the Organometallic Complexes 1187 IV. Synthetic Approaches to the 7-Azabicyclo[2.2.1]heptanes 1187 A. Intramolecular Cyclization of Cyclohexylamine Derivatives 1187 B. Reduction of 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes 1188 C. [3+2] Cycloaddition Reactions 1189 D. Intramolecular Cyclization of Substituted Proline Derivatives 1189 E. Miscellaneous Reactions 1190 V. Properties of 7-Azabicyclo[2.2.1]heptane Derivatives 1190 A. 7-Azabicyclo[2.2.1]heptane and 7-Azabicyclo-[2.2.1]heptene Derivatives as Potential Chemotherapeutic Drugs 1190

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“…Compound 133 was also found to react with dialkyl acetylenedicarboxylates to give tetraalkyl 7-azabicyclo[2.2.1]hept-2-ene-1,2,3,4-carboxylates. 130 1-Iodo-2-acetoxy- heptane derivative designed and synthesized as a potential biological agent. 109 The cocaine analogue 106 was prepared to investigate the structureactivity relationships (SAR) of local anesthetics.…”

Section: E Miscellaneous Reactionsmentioning

confidence: 99%

“…Compound 133 was also found to react with dialkyl acetylenedicarboxylates to give tetraalkyl 7-azabicyclo[2.2.1]hept-2-ene-1,2,3,4-carboxylates. 130 1-Iodo-2-acetoxy-8-methyl-8-azabicyclo[3.2.1]octan-3-one (136) was reductively transformed into 7-azabicyclo[2.2.1]heptane (137) with lithium aluminum hydride. 131 The structural assignment of the 1-(hydroxymethyl)-2R-hydroxy-7-methyl-7-azabicyclo-[2.2.1]heptane (137) was determined spectroscopically (IR, NMR, and mass spectrometry) and by chemical transformation into 1-methyl-2R-hydroxy-7-methyl-7-azabicyclo[2.2.1]heptane 138 (Scheme 34).…”

Section: E Miscellaneous Reactionsmentioning

confidence: 99%

Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes

1996

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“…7 These compounds undergo an interesting photocyclization to 3,4-dihydropyrroles which can be intercepted, as 1,3-dipoles, in cycloaddition reactions with alkenes and alkynes. 6,7,8 Compound 14a is also reported to react as an electrophile with hydrazines 9 and with primary amines, 10 giving hydrazones and imines of methyl pyruvate as products. The diester 14a reacts with DDQ to give a single product in high yield, a 1:1 adduct of the diester and DDQ (15), which structure was established by X-ray crystallography.…”

Section: Methodsmentioning

confidence: 99%

Exploiting azafulvenium methides chemistry

Melo¹

2006

Arkivoc

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“…Other cross-conjugated bis(enamines) of this type have been produced by thermal rearrangement of vinylaziridines . These compounds undergo an interesting photocyclization to 3,4-dihydropyrroles that can be intercepted, as 1,3-dipoles, in cycloaddition reactions with alkenes and alkynes. 2b,, Compound 3a is also reported to react as an electrophile with hydrazines and with primary amines, giving hydrazones and imines of methyl pyruvate as products.…”

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confidence: 99%

A New Route to Cross-Conjugated Bis(enamines) and an Unusual Reaction with DDQ

et al. 1999

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In previous papers, we reported that thiazolidines derived from cysteine methyl ester and aldehydes react with silver carbonate and DBU; the reactions produce transient 1-substituted methyl 2-azadiene-3-carboxylates that act as dienes in the Diels-Alder reaction. 1 When we apply the same procedure to the thiazolidines 1a-d we find that the products are isolable cross-conjugated bis(enamines) 3a-d, the more stable tautomers of the azadienes 2a-d (Scheme 1). This is a new versatile route to enamines of this type.The diester 3a is a known compound that has previously been prepared from methyl -halo-R-aminopropionate hydrohalides by reaction with bases; 2 compounds 3b-d are previously unknown. Other cross-conjugated bis(enamines) of this type have been produced by thermal rearrangement of vinylaziridines. 3 These compounds undergo an interesting photocyclization to 3,4-dihydropyrroles that can be intercepted, as 1,3-dipoles, in cycloaddition reactions with alkenes and alkynes. 2b,3,4 Compound 3a is also reported to react as an electrophile with hydrazines 5 and with primary amines, 6 giving hydrazones and imines of methyl pyruvate as products.In an attempt to cyclize the diester 3a directly to dimethyl pyrrole-2,5-dicarboxylate by using DDQ as an oxidant, a single product was isolated in high yield.Instead of the pyrrole, it proved to be an interesting 1:1 adduct of the diester and DDQ whose structure 4 was established for the compound by X-ray crystallography (Figure 1).The X-ray analysis clearly shows that the C9-C10-N1-C2-C3-C4 and C4-C5-C6-C7-C8-C9 rings are fused cis around the common C4-C9 bond and are furthermore linked by the methylenic bridge C10-C11-C5. The conformation of the two above-mentioned rings is intermediate between E 1 envelope and 1 H 2 half-chair, as shown by the ring puckering parameters 7 Q ) 0.662-The conformation of the bridging ring C4-C5-C11-C10-C9 is very close to 5 T 1 (twisted around the C4-C9 bond), as shown by the puckering parameters Q(2) ) 0.566(4) Å, φ(2) ) 163.3(4)°. The H1 atom is shared in a bifurcated intramolecular hydrogen bond [N1-H1‚‚‚O1: 2.714(4) Å; N1-H1‚‚‚O4: 2.677(5) Å, sum of the valence angles around H1 ) 358.2°]. The methoxycarbonyl group attached to the sp 2 C2 atom is almost coplanar with the plane defined by the C10-N1-C2 atoms, whereas the other methoxycarbonyl group that is attached to the tetrahedric C10 atom is twisted by -16.9(5)°around the C10-C12 single bond. The H5 atom of the hydroxyl group is also involved in a bifurcated † Departamento de Química. ‡ Departamento de Física. (1) (a) Gilchrist, T. L.; Rocha Gonsalves, A. M. d'A.; Pinho e Melo, T. M. V. D. Tetrahedron 1994, 50, 13709-13724. (b) Pinho e Melo, T.

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Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes

Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes

Exploiting azafulvenium methides chemistry

A New Route to Cross-Conjugated Bis(enamines) and an Unusual Reaction with DDQ

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