PMID- 26226194
OWN - NLM
STAT- MEDLINE
DCOM- 20160629
LR  - 20150914
IS  - 2156-8944 (Electronic)
IS  - 2156-8944 (Linking)
VI  - 17
IP  - 9
DP  - 2015 Sep 14
TI  - Leuckart-Wallach Route Toward Isocyanides and Some Applications.
PG  - 493-9
LID - 10.1021/acscombsci.5b00066 [doi]
AB  - Isocyanide-based multicomponent reactions (IMCR) are among the most important 
      chemical reactions to efficiently generate molecular diversity and have found 
      widespread use in industry and academia. Generally, isocyanides are synthesized 
      in 1-2 steps starting from primary amines. Here, we provide experimental detail 
      on an alternative approach toward formamides and, thus, isocyanides via the 
      Leuckart-Wallach reaction in an improved variation. The resulting >50 synthesized 
      and characterized formamides are useful starting materials for IMCR, as well as 
      other chemistries. The advantage of using the Leuckart-Wallach pathway to 
      formamides and isocyanides is the lower price, on average, of the starting 
      materials, as well as their differential and complementary structural diversity, 
      as compared to the primary amine pathway.
FAU - Neochoritis, Constantinos G
AU  - Neochoritis CG
AD  - Department of Drug Design, University of Groningen , A. Deusinglaan 1, Groningen 
      9700AV, The Netherlands.
FAU - Zarganes-Tzitzikas, Tryfon
AU  - Zarganes-Tzitzikas T
AD  - Department of Drug Design, University of Groningen , A. Deusinglaan 1, Groningen 
      9700AV, The Netherlands.
FAU - Stotani, Silvia
AU  - Stotani S
AD  - Department of Drug Design, University of Groningen , A. Deusinglaan 1, Groningen 
      9700AV, The Netherlands.
FAU - Domling, Adrian
AU  - Domling A
AD  - Carmolex, Inc. , Pittsburgh, Pennsylvania 15219, United States.
FAU - Herdtweck, Eberhardt
AU  - Herdtweck E
AD  - Institut fur Anorganische Chemie, Technische Universitat Munchen , 80333 Munchen, 
      Germany.
FAU - Khoury, Kareem
AU  - Khoury K
AD  - Carmolex, Inc. , Pittsburgh, Pennsylvania 15219, United States.
FAU - Domling, Alexander
AU  - Domling A
AD  - Department of Drug Design, University of Groningen , A. Deusinglaan 1, Groningen 
      9700AV, The Netherlands.
LA  - eng
GR  - 1P41GM094055/GM/NIGMS NIH HHS/United States
GR  - 1R01GM097082/GM/NIGMS NIH HHS/United States
GR  - 1R21GM087617/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
DEP - 20150810
PL  - United States
TA  - ACS Comb Sci
JT  - ACS combinatorial science
JID - 101540531
RN  - 0 (Amines)
RN  - 0 (Cyanides)
RN  - 0 (Formamides)
RN  - 0 (Indicators and Reagents)
SB  - IM
MH  - Amines/chemistry
MH  - Costs and Cost Analysis
MH  - Cyanides/*chemical synthesis
MH  - Formamides/chemical synthesis
MH  - Indicators and Reagents
MH  - Magnetic Resonance Spectroscopy
OTO - NOTNLM
OT  - IMCR
OT  - Leuckart-Wallach
OT  - Ugi
OT  - formamides
OT  - isocyanides
EDAT- 2015/08/01 06:00
MHDA- 2016/06/30 06:00
CRDT- 2015/07/31 06:00
PHST- 2015/07/31 06:00 [entrez]
PHST- 2015/08/01 06:00 [pubmed]
PHST- 2016/06/30 06:00 [medline]
AID - 10.1021/acscombsci.5b00066 [doi]
PST - ppublish
SO  - ACS Comb Sci. 2015 Sep 14;17(9):493-9. doi: 10.1021/acscombsci.5b00066. Epub 2015 
      Aug 10.