{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T07:15:38Z","timestamp":1788419738197,"version":"build-2803163510"},"reference-count":26,"publisher":"American Chemical Society (ACS)","issue":"3","license":[{"start":{"date-parts":[[2017,3,13]],"date-time":"2017-03-13T00:00:00Z","timestamp":1489363200000},"content-version":"vor","delay-in-days":32,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccbyncnd_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["2R01GM097082-05"],"award-info":[{"award-number":["2R01GM097082-05"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004543","name":"China Scholarship Council","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004543","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004963","name":"Seventh Framework Programme","doi-asserted-by":"publisher","award":["115489"],"award-info":[{"award-number":["115489"]}],"id":[{"id":"10.13039\/501100004963","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["POIG.02.01.00-12-023\/08"],"award-info":[{"award-number":["POIG.02.01.00-12-023\/08"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2017,3,13]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>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\u2019s diversity. Here, we describe the use of N-Boc protected hydrazine together with \u03b1-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\u201387%.<\/jats:p>","DOI":"10.1021\/acscombsci.7b00009","type":"journal-article","created":{"date-parts":[[2017,2,9]],"date-time":"2017-02-09T10:36:29Z","timestamp":1486636589000},"page":"193-198","source":"Crossref","is-referenced-by-count":24,"title":["Two Cycles with One Catch: Hydrazine in Ugi 4-CR\nand Its Postcyclizations"],"prefix":"10.1021","volume":"19","author":[{"given":"Yuanze","family":"Wang","sequence":"first","affiliation":[{"name":"University of Groningen , , A. Deusinglaan 1 , ,","place":["Groningen, The Netherlands, 9713 AV"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0903-8174","authenticated-orcid":true,"given":"Pravin","family":"Patil","sequence":"additional","affiliation":[{"name":"University of Groningen , , A. Deusinglaan 1 , ,","place":["Groningen, The Netherlands, 9713 AV"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katarzyna","family":"Kurpiewska","sequence":"additional","affiliation":[{"name":"Jagiellonian University , , Ingardena 3 , ,","place":["Krakow, Poland, 30-060"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Justyna","family":"Kalinowska-Tluscik","sequence":"additional","affiliation":[{"name":"Jagiellonian University , , Ingardena 3 , ,","place":["Krakow, Poland, 30-060"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9923-8873","authenticated-orcid":true,"given":"Alexander","family":"Do\u0308mling","sequence":"additional","affiliation":[{"name":"University of Groningen , , A. Deusinglaan 1 , ,","place":["Groningen, The Netherlands, 9713 AV"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2017,2,9]]},"reference":[{"key":"2026090302380887900_cit1","doi-asserted-by":"publisher","first-page":"603","DOI":"10.1038\/nrd4596","article-title":"Big opportunities for\nsmall molecules in immuno-oncology","volume":"14","author":"Adams","year":"2015","journal-title":"Nat. Rev.\nDrug Discovery"},{"key":"2026090302380887900_cit2","doi-asserted-by":"publisher","first-page":"4640","DOI":"10.1021\/cr4004049","article-title":"Small molecule modulators of protein\u2013protein\ninteractions: selected case studies","volume":"114","author":"Aeluri","year":"2014","journal-title":"Chem. Rev."},{"key":"2026090302380887900_cit3","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1016\/j.cbpa.2015.10.032","article-title":"Advances in discovering\nsmall molecules to probe protein function in a systems context","volume":"30","author":"Doyle","year":"2016","journal-title":"Curr. Opin. Chem. Biol."},{"key":"2026090302380887900_cit4","doi-asserted-by":"publisher","first-page":"1102","DOI":"10.1016\/j.chembiol.2014.09.001","article-title":"Small-molecule inhibitors\nof protein-protein\ninteractions: progressing toward the reality","volume":"21","author":"Arkin","year":"2014","journal-title":"Chem. Biol."},{"key":"2026090302380887900_cit5a","doi-asserted-by":"publisher","first-page":"181","DOI":"10.1016\/j.drudis.2014.08.014","article-title":"The joint\neuropean compound library: Boosting precompetitive research","volume":"20","author":"Besnard","year":"2015","journal-title":"Drug Discovery Today"},{"key":"2026090302380887900_cit5b","doi-asserted-by":"publisher","first-page":"1310","DOI":"10.1016\/j.drudis.2015.09.009","article-title":"Expansion of chemical space for collaborative lead generation and\ndrug discovery: the European Lead Factory Perspective","volume":"20","author":"Hamza","year":"2015","journal-title":"Drug Discovery Today"},{"key":"2026090302380887900_cit5c","doi-asserted-by":"publisher","first-page":"173","DOI":"10.1038\/nrd3956","article-title":"European lead\nfactory opens for business","volume":"12","author":"Mullard","year":"2013","journal-title":"Nat. Rev. Drug Discovery"},{"key":"2026090302380887900_cit5d","doi-asserted-by":"publisher","first-page":"2613","DOI":"10.1016\/j.bmc.2015.02.046","article-title":"Innovative approaches to the design\nand synthesis of small molecule libraries","volume":"23","author":"Nelson","year":"2015","journal-title":"Bioorg.\nMed. Chem."},{"key":"2026090302380887900_cit5e","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/j.drudis.2015.11.005","article-title":"The ELF Honest Data Broker: informatics\nenabling public\u2013private collaboration in a precompetitive arena","volume":"21","author":"Paillard","year":"2016","journal-title":"Drug Discovery Today"},{"key":"2026090302380887900_cit6","doi-asserted-by":"publisher","first-page":"17","DOI":"10.1021\/cr0505728","article-title":"Recent developments\nin isocyanide based multicomponent reactions in applied chemistry","volume":"106","author":"Domling","year":"2006","journal-title":"Chem. Rev."},{"key":"2026090302380887900_cit7","doi-asserted-by":"publisher","first-page":"3083","DOI":"10.1021\/cr100233r","article-title":"Chemistry and biology of multicomponent\nreactions","volume":"112","author":"Do\u0308mling","year":"2012","journal-title":"Chem. Rev."},{"key":"2026090302380887900_cit8","doi-asserted-by":"crossref","DOI":"10.1002\/3527605118","volume-title":"Multicomponent\nReactions","author":"Zhu","year":"2005"},{"key":"2026090302380887900_cit9","doi-asserted-by":"publisher","first-page":"4792","DOI":"10.1039\/c3ob40523k","article-title":"Various cyclization\nscaffolds by a truly Ugi 4-CR","volume":"11","author":"Sinha","year":"2013","journal-title":"Org. Biomol.\nChem."},{"key":"2026090302380887900_cit10","doi-asserted-by":"publisher","first-page":"5736","DOI":"10.1021\/ol5024882","article-title":"A Universal\nIsocyanide for Diverse Heterocycle Syntheses","volume":"16","author":"Patil","year":"2014","journal-title":"Org. Lett."},{"key":"2026090302380887900_cit11","doi-asserted-by":"publisher","first-page":"2699","DOI":"10.1016\/j.bmc.2014.12.021","article-title":"MCR synthesis\nof a tetracyclic tetrazole scaffold","volume":"23","author":"Patil","year":"2015","journal-title":"Bioorg.\nMed. Chem."},{"key":"2026090302380887900_cit12","doi-asserted-by":"publisher","first-page":"51","DOI":"10.1002\/ejoc.201403401","article-title":"Concise Synthesis of Tetrazole\u2013Ketopiperazines\nby Two Consecutive Ugi Reactions","volume":"2015","author":"Zarganes-Tzitzikas","year":"2015","journal-title":"Eur. J. Org.\nChem."},{"key":"2026090302380887900_cit13","doi-asserted-by":"publisher","first-page":"3109","DOI":"10.1021\/jo900210x","article-title":"Ugi-post functionalization, from\na single set of Ugi-adducts to two distinct heterocycles by microwave-assisted\npalladium-catalyzed cyclizations: tuning the reaction pathways by\nligand switch","volume":"74","author":"Erb","year":"2009","journal-title":"J. Org. Chem."},{"key":"2026090302380887900_cit14a","doi-asserted-by":"publisher","first-page":"4959","DOI":"10.1016\/S0040-4039(01)00919-4","article-title":"Two-step solution-phase synthesis\nof novel benzimidazoles utilizing a UDC (Ugi\/de-Boc\/cyclize) strategy","volume":"42","author":"Tempest","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"2026090302380887900_cit14b","doi-asserted-by":"publisher","first-page":"3681","DOI":"10.1016\/S0040-4039(02)00636-6","article-title":"Short solution\nphase preparation of fused azepine-tetrazoles via a UDC (Ugi\/de-Boc\/cyclize)\nstrategy","volume":"43","author":"Nixey","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"2026090302380887900_cit14c","doi-asserted-by":"publisher","first-page":"5606","DOI":"10.1016\/j.tet.2012.04.068","article-title":"Synthesis of tetrazolo-fused benzodiazepines and benzodiazepinones\nby a two-step protocol using an Ugi-azide reaction for initial diversity\ngeneration","volume":"68","author":"Gunawan","year":"2012","journal-title":"Tetrahedron"},{"key":"2026090302380887900_cit14d","doi-asserted-by":"publisher","first-page":"460","DOI":"10.1021\/co300046r","article-title":"General one-pot,\ntwo-step protocol accessing a range of novel polycyclic heterocycles\nwith high skeletal diversity","volume":"14","author":"Xu","year":"2012","journal-title":"ACS Comb. Sci."},{"key":"2026090302380887900_cit15","doi-asserted-by":"publisher","first-page":"1122","DOI":"10.1055\/s-0035-1561353","article-title":"Hydrazine\nin the Ugi Tetrazole Reaction","volume":"48","author":"Patil","year":"2016","journal-title":"Synthesis"},{"key":"2026090302380887900_cit16a","doi-asserted-by":"publisher","first-page":"3281","DOI":"10.1021\/ol048850x","article-title":"Titanium\ncatalysis in the Ugi reaction of \u03b1-amino acids with aromatic\naldehydes","volume":"6","author":"Godet","year":"2004","journal-title":"Org. Lett."},{"key":"2026090302380887900_cit16b","doi-asserted-by":"publisher","first-page":"12866","DOI":"10.1016\/j.tet.2007.10.050","article-title":"Lewis acid-catalyzed formation of\nUgi four-component reaction product from Passerini three-component\nreaction system without an added amine","volume":"63","author":"Dai","year":"2007","journal-title":"Tetrahedron"},{"key":"2026090302380887900_cit16c","doi-asserted-by":"publisher","first-page":"3678","DOI":"10.1002\/ejoc.200800340","article-title":"The Effect of Lewis Acids on the\nStereochemistry in the Ugi Three-Component Reaction with D-lyxo-Pyrroline","volume":"2008","author":"Bonger","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"2026090302380887900_cit16d","doi-asserted-by":"publisher","first-page":"3957","DOI":"10.1002\/ejoc.201500270","article-title":"Diversity-Oriented Synthesis of \u03b2-Lactams and\n\u03b3-Lactams by Post-Ugi Nucleophilic Cyclization: Lewis Acids\nas Regioselective Switch","volume":"2015","author":"Li","year":"2015","journal-title":"Eur. J. Org. Chem."}],"container-title":["ACS Combinatorial Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acscombsci.7b00009","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsccc\/article-pdf\/19\/3\/193\/67158610\/acscombsci.7b00009.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsccc\/article-pdf\/19\/3\/193\/67158610\/acscombsci.7b00009.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T06:38:12Z","timestamp":1788417492000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsccc\/article\/19\/3\/193\/685783\/Two-Cycles-with-One-Catch-Hydrazine-in-Ugi-4-CR"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,9]]},"references-count":26,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2017,2,9]]},"published-print":{"date-parts":[[2017,3,13]]}},"URL":"https:\/\/doi.org\/10.1021\/acscombsci.7b00009","relation":{},"ISSN":["2156-8952","2156-8944"],"issn-type":[{"value":"2156-8952","type":"print"},{"value":"2156-8944","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,2,9]]}}}