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Synthesis of Five-Membered Heterocycles Through β-Lactam Ring-Expansion Reaction

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Beta-Lactams

Abstract

The β-lactam ring (2-azetidinone) is found in classical antibiotics such as penicillins and cephalosporins. In addition, this fragment is also detected in compounds with other pharmacological profile, such as antidiabetic, anticancer and cholesterol absorption inhibition among others. Besides, to its biological relevance, the β-lactam ring is a versatile building block for the synthesis of a huge amount of acyclic and cyclic structures by selective fragmentation or rearrangement of each single bond. This chapter is devoted to the synthesis of five-membered heterocycles by ring expansion of β-lactams. The contributions presented in this chapter have been selected from the developments achieved mainly in the last 20 years, in addition to some remarkable early reports.

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Abbreviations

Ac:

Acetyl

AIBN:

2,2′-Azobisisobutyronitrile

Boc:

t-Butoxycarbonyl

CAN:

Cerium(IV) ammonium nitrate

Cbz:

Benzyloxycarbonyl

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCE:

1,1-Dichloroethane

DIAD:

Diisopropyl azodicarboxylate

DMF:

N,N-Dimethylformamide

DMP:

Dess-Martin periodinane

DMS:

Dimethylsulfoxide

HMPA:

Hexamethylphosphoramide

IPr:

1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene

Naph:

Naphthyl

NBS:

N-Bromosuccinimide

NIS:

N-Iodosuccinimide

Nu:

Nucleophile

Phth:

Phthaloyl

PMP:

p-Methoxyphenyl

PMB:

p-Methoxybenzyl

PTSA:

p-Toluenesulfonic acid

Py:

Pyridine (pyridyl)

TBACN:

Tetrabutylammonium cyanide

TBCA:

Tribromoisocyanuric acid

TBS:

t-Butyldimethylsilyl

THF:

Tetrahydrofuran

TMS:

Trimethylsilyl

Tph:

2-Thiophenyl

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Authors and Affiliations

  1. Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040, Madrid, Spain

    Benito Alcaide & Cristina Aragoncillo

  2. Instituto de Química Orgánica General, IQOG-CSIC, Juan de la Cierva 3, 28006, Madrid, Spain

    Pedro Almendros

Authors
  1. Benito Alcaide
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  2. Pedro Almendros
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  3. Cristina Aragoncillo
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Corresponding authors

Correspondence to Benito Alcaide , Pedro Almendros or Cristina Aragoncillo .

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Editors and Affiliations

  1. Community Health System of South Texas, Edinburg, Texas, USA

    Bimal K. Banik

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Alcaide, B., Almendros, P., Aragoncillo, C. (2017). Synthesis of Five-Membered Heterocycles Through β-Lactam Ring-Expansion Reaction. In: Banik, B. (eds) Beta-Lactams. Springer, Cham. https://doi.org/10.1007/978-3-319-55621-5_6

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