PMID- 28181791
OWN - NLM
STAT- MEDLINE
DCOM- 20171011
LR  - 20181113
IS  - 2156-8944 (Electronic)
IS  - 2156-8952 (Print)
IS  - 2156-8944 (Linking)
VI  - 19
IP  - 3
DP  - 2017 Mar 13
TI  - Two Cycles with One Catch: Hydrazine in Ugi 4-CR and Its Postcyclizations.
PG  - 193-198
LID - 10.1021/acscombsci.7b00009 [doi]
AB  - Isocyanide-based multicomponent reactions (IMCR) are by far the most versatile 
      reactions that can construct relatively complex molecules by one-pot synthesis. 
      More importantly, the development of post IMCR modifications significantly 
      improves the scaffold's diversity. Here, we describe the use of N-Boc protected 
      hydrazine together with alpha-amino acid derived isocyanides in the Ugi tetrazole 
      reaction and its post cyclization under both acidic and basic conditions. The 
      cyclization in acidic conditions was conducted in a one pot fashion, which give 
      7-aminotetrazolopyrazinone (6) and tetrazolotriazepinone (7) cyclic products. The 
      post cyclization under basic condition could selectively afford Boc-protected 
      7-aminotetrazolopyrazinone (8) products in yield of 38-87%.
FAU - Wang, Yuanze
AU  - Wang Y
AD  - University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV 
      Groningen, The Netherlands.
FAU - Patil, Pravin
AU  - Patil P
AUID- ORCID: 0000-0002-0903-8174
AD  - University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV 
      Groningen, The Netherlands.
FAU - Kurpiewska, Katarzyna
AU  - Kurpiewska K
AD  - Jagiellonian University , Faculty of Chemistry, Department of Crystal Chemistry 
      and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Krakow, 
      Poland.
FAU - Kalinowska-Tluscik, Justyna
AU  - Kalinowska-Tluscik J
AD  - Jagiellonian University , Faculty of Chemistry, Department of Crystal Chemistry 
      and Crystal Physics, Biocrystallography Group, Ingardena 3, 30-060 Krakow, 
      Poland.
FAU - Domling, Alexander
AU  - Domling A
AUID- ORCID: 0000-0002-9923-8873
AD  - University of Groningen , Department of Drug Design, A. Deusinglaan 1, 9713 AV 
      Groningen, The Netherlands.
LA  - eng
GR  - R01 GM097082/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 - 20170217
PL  - United States
TA  - ACS Comb Sci
JT  - ACS combinatorial science
JID - 101540531
RN  - 0 (3-aminopyrazinone)
RN  - 0 (Cyanides)
RN  - 0 (Hydrazines)
RN  - 0 (Pyrazines)
RN  - 0 (Tetrazoles)
SB  - IM
MH  - Combinatorial Chemistry Techniques
MH  - Cyanides/chemical synthesis/*chemistry
MH  - Cyclization
MH  - Hydrazines/chemical synthesis/*chemistry
MH  - Models, Molecular
MH  - Pyrazines/chemical synthesis/chemistry
MH  - Tetrazoles/*chemical synthesis/chemistry
PMC - PMC5350607
OTO - NOTNLM
OT  - European Lead Factory
OT  - hydrazine
OT  - isocyanide-based multicomponent reactions
OT  - one-pot synthesis
OT  - post cyclization
OT  - scaffolds diversity
OT  - tetrazole
COIS- The authors declare no competing financial interest.
EDAT- 2017/02/10 06:00
MHDA- 2017/10/12 06:00
PMCR- 2017/03/15
CRDT- 2017/02/10 06:00
PHST- 2017/02/10 06:00 [pubmed]
PHST- 2017/10/12 06:00 [medline]
PHST- 2017/02/10 06:00 [entrez]
PHST- 2017/03/15 00:00 [pmc-release]
AID - 10.1021/acscombsci.7b00009 [doi]
PST - ppublish
SO  - ACS Comb Sci. 2017 Mar 13;19(3):193-198. doi: 10.1021/acscombsci.7b00009. Epub 
      2017 Feb 17.