Studies on pyrrolizidines and related compounds. Part 9. Rearrangement of 7a-trichloromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine and related compounds: an alternative route to 5-substituted 1-azabicyclo[3.3.1]nonanes

Miyano, Seiji; Mibu, Nobuko; Irie, M.; Fujii, Shin-ichiro; Fujisaki, Fumiko; Abe, Nobuhiro; Sumoto, Kunihiro

doi:10.1039/p19870000313

Cited by 6 publications

(9 citation statements)

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“…Subsequently, Miyano and coworkers studied a related rearrangement in the 1-azabicyclo[3.3.1]nonane system (Scheme 59). 353,354 In their case, the reaction was carried out step-wise and the trichloromethyl analogue 227 was isolated. 353 This intermediate then underwent rearrangement to 1-azabicyclo[3.3.1]nonane 229 upon heating in pyridine.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%

“…353,354 In their case, the reaction was carried out step-wise and the trichloromethyl analogue 227 was isolated. 353 This intermediate then underwent rearrangement to 1-azabicyclo[3.3.1]nonane 229 upon heating in pyridine. Hydrolysis to the corresponding bridged lactam has not been reported for this example.…”

Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%

“…409–412,102 Although several bridgehead imines and iminium ions have been reported, 413–419 only a few of these compounds bear nitrogen atom at the bridgehead position in a bicyclic system. 420–424,353,354 …”

Section: Synthesis Of Bridged Lactams With Complex Ring Systems Anmentioning

confidence: 99%

“…Aziridinium ions are known to undergo regioselective ring-opening with a wide range of nucleophiles, and this type of rearrangement has been used extensively to make planar nitrogen-containing heterocycles. , In 1970, Arata reported the synthesis of bridged lactam 225 , containing a [4.4.1] ring system via aziridinium rearrangement using a one-pot protocol (Scheme ). , The proposed mechanism is outlined in Scheme , and it involves the following steps: (1) tautomerization of enamine 224 to iminium ion, (2) addition of the trichloromethyl moiety, (3) formation of the aziridinium 224b , (4) regioselective nucleophilic ring-opening to the trichloroderivative 224c , and (5) hydrolysis to give the bridged lactam 225 . Subsequently, Miyano and co-workers studied a related rearrangement in the 1-azabicyclo[3.3.1]nonane system (Scheme ). , In their case, the reaction was carried out stepwise and the trichloromethyl analogue 227 was isolated . This intermediate then underwent rearrangement to 1-azabicyclo[3.3.1]nonane 229 upon heating in pyridine.…”

Section: Synthesis Of Bridged Lactams With the N–(co) Bond On A One-c...mentioning

confidence: 99%

“…Iminium ions containing nitrogen atom at the bridgehead position cannot achieve full resonance stabilization and are typically considered as carbocations. − , Although several bridgehead imines and iminium ions have been reported, − only a few of these compounds bear a nitrogen atom at the bridgehead position in a bicyclic system. − ,, …”

Section: Synthesis Of Bridged Lactams With Complex Ring Systems and R...mentioning

confidence: 99%

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Chemistry of Bridged Lactams and Related Heterocycles

2013

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CONTENTS 1. Introduction 5702 2. General Properties of Bridged Lactams 5703 2.1. Distortion Parameters of Bridged Lactams 5703 2.2. Bond Lengths of Bridged Lactams 5703 2.3. Spectroscopic Properties of Bridged Lactams 5703 2.4. Analogy of Bridged Lactams to Bridgehead Olefins 5704 2.5. Chemical and Biological Significance of Distorted Amides 5704 3. Synthesis of Historically Important Bridged Lactams 5704 3.1. Quinuclidone Derivatives 5704 3.2. Adamantanone Derivatives 5707 4. Synthesis of Bridged Lactams with the N−(CO) Bond on a Two-Carbon or Larger Bridge, ([m. (≥2).n] Type) 5708 4.1. Condensation Reactions Forming the N− C(O) Bond 5708 4.2. Heck Reactions 5711 4.3. Diels−Alder Reactions 5712 4.4. Carbene Insertion Reactions 5713 4.5. Reactions via Radical Intermediates 5714 4.6. Miscellaneous Examples 5714 5. Synthesis of Bridged Lactams with the N−(CO) Bond on a One-Carbon Bridge, ([m.1.n] Type) 5715 5.1. Carbene Insertion Reactions 5715 5.2. Schmidt Reactions 5716 5.3.

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Section: Synthesis Of Bridged Lactams With N–(co) Bond On One-carbmentioning

confidence: 99%