Azaindole derivatives

Yakhontov, L. N.; Lapan, E. I.; Rubtsov, M. V.

doi:10.1007/bf00471161

Cited by 1 publication

(2 citation statements)

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“…279 Although the yield was very low, lactam 96 could be separated from the polymer 97 by sublimation from the reaction mixture. The condensation of the corresponding acid chloride using a protocol developed by Yakhontov and Pracejus for the synthesis of 2-quinuclidones (Schemes 3–5) 252–258 was unsuccessful in this case. Based on its infrared stretching frequency of 1680 cm −1 , stability in water, and moderate tendency to undergo polymerization, Hall proposed lactam 96 to be only slightly distorted from planarity.…”

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

confidence: 99%

“…252 However, the isolation of the bridged lactam 18 as reported by Yakhontov has been questioned in the literature on several occasions 253,254,107 because of the propensity of unsubstituted quinuclidin-2-ones to polymerize, vigorous conditions utilized for the synthesis of lactam 18 and the lack of any characterization data save elemental analysis of nitrogen. 252 …”

Section: Synthesis Of Historically Important Bridged Lactamsmentioning

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 Two-carbmentioning

confidence: 99%