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Ammonia synthons for the multicomponent assembly of complex gamma-lactams.

ABSTRACT: The synthesis of ?-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.

SUBMITTER: Tan DQ

PROVIDER: S-EPMC3084106 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Ammonia synthons for the multicomponent assembly of complex gamma-lactams.

Tan Darlene Q DQ Martin Kevin S KS Fettinger James C JC Shaw Jared T JT

Proceedings of the National Academy of Sciences of the United States of America 20110202 17

The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N-functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitr ...[more]

PMID: 21289284

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