Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 22, Pages 11450-11469Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402010b
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Funding
- National Science Foundation [CHE-1111567]
- National Institutes of Health [GM 28273]
- Merck Research Laboratories
- Boehringer Ingelheim Pharmaceuticals
- AstraZeneca Graduate Fellowship
- David A. Johnson, Merck, and George Buchi Summer Fellowships
- C. P. Chu and Y. Lai Fund
- Eli Lilly Graduate Fellowship
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1111567] Funding Source: National Science Foundation
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Highly substituted polycyclic aromatic and heteroaromatic compounds are produced via a two-stage tandem benzannulation/cyclization strategy. The initial benzannulation step proceeds via a pericyclic cascade mechanism triggered by thermal or photochemical Wolff rearrangement of a diazo ketone. The photochemical process can be performed using a continuous flow reactor which facilitates carrying out reactions on a large scale and minimizes the time required for photolysis. Carbomethoxy ynamides as well as more ketenophilic bis-silyl ynamines and N-sulfonyl and N-phosphoryl ynamides serve as the reaction partner in the benzannulation step. In the second stage of the strategy, RCM generates benzofused nitrogen heterocycles, and various heterocyclization processes furnish highly substituted and polycyclic indoles of types that were not available by using the previous cyclobutenone-based version of the tandem strategy.
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